,,BRL ,,CODE ,,=
,,*EMICAL ,,NOT,N
#AIIG
,DEVELOP$ ,"U ! ,SPONSOR%IP (!
,,BRL ,,AU?OR;Y ,,(
,,NOR? ,,AM]ICA
,PUBLI%$ BY
,AM]ICAN ,PR9T+ ,H\SE =! ,BL
,L\ISVILLE1 ,K5TUCKY
,COPY"R1 #AIIG1 BY
,! ,,BRL ,AU?OR;Y ( ,NOR? ,AM]ICA
,? MAT]IAL MAY 2 DUPLICAT$
B N ALT]$4
,TRANSCRIB$1 #AIIH1 BY
,VON ,E4 ,EUL]T
,AM]ICAN ,R$ ,CROSS ,BRL ,S]VICE
,WI*ITA1 ,KANSAS
,9 ,?REE ,VOLUMES
,VOLUME #A
,BRL PAGES P#A-P#H & #A-HB
,PR9T PAGES ;I-;IX & #A-EB P#A ,,BANA ,,MEMB]S
,AM]ICAN ,C\NCIL (! ,BL (,A,C,B)
,AM]ICAN ,F.D,N =! ,BL (,A,F,B)
,AM]ICAN ,PR9T+ ,H\SE =! ,BL (,A,P,H)
,ASSOCIAT$ ,S]VICES =! ,BL (,A,S,B)
,ASSOIC,N =! ,$UC,N & ,REHABILIT,N (!
,BL & ,VISU,Y ,IMPAIR$ (,A,E,R)
,CALI=NIA ,TRANSCRIB]S & ,$UCATORS (!
,VISU,Y ,H&ICAPP$ (,C,T,E,V,H)
,! ,CANADIAN ,N,NAL ,9/ITUTE =! ,BL
(,,C,N,I,B)
,! ,CLOV]NOOK ,C5T]3 ,OPPORTUNITIES =!
,BL (,C,C,O,B)
,N,NAL ,BRL ,ASSCI,N1 ,9C4 (,N,B,A)
,N,NAL ,BRL ,PRESS ,9C4 (,N,B,P)
,N,NAL ,F$],N (! ,BL (,N,F,B)
,N,NAL ,LIBR>Y ,S]VICE =! ,BL &
,PHYSIC,Y ,H&ICAPP$1 ,LIBR>Y ( ,3GRESS
(,N,L,S_/,B,P,H)
,ROYAL ,NEW ,Z1L& ,F.D,N =! ,BL
(,R,N,Z,F,B), ,ASSOICATE ,MEMB]
,CATALOG #E-AFIJJ-JJ ,,3T5TS
,,VOLUME #1
,PAGE
,PREFACE """""""""""""""""""""""""" ;VII
,9TRODUC;N """"""""""""""""""""""""" ;IX
#1 ,,BRL ,,9DICATORS """""""""""""""" #1
#1.1 ,3/RUC;N (A ,HORIZONTAL ,BOND #1
#1.2 ,RUNOV] ,LOCATOR """"""""""""" #1
#1.3 ,SPAC+ """"""""""""""""""""""" #1
#1.4 ,PUNCTU,N """""""""""""""""""" #2
#2 ,,G5]AL ,,=MAT """"""""""""""""""" #3
#2.1 ,RUNOV] ,SITES """"""""""""""" #3
#2.2 ,PREF];E ,LI/ = ,RUNOV]S """"" #3
#2.3 ,L9K$ ,EXPRES.NS """"""""""""" #3
#2.4 ,4PLAY$ ,EXPRES.NS ,3TA9+ ,NO
,L9KS """"""""""""""""""""""""" #4
#2.5 ,RUNOV]S ( ,L9E> & ,SPATIAL
,=MULAS """"""""""""""""""""""" #4
#2.6 ,SPATIAL ,MAT]IAL """""""""""" #6
#2.7 ,C.ELL,N """""""""""""""""""" #10
#3 ,,*EMICAL ,,SIGNS ,,& ,,SYMBOLS #11
P#C #3.1 ,*EMICAL ,>R[S """""""""""""" #11
#3.2 ,BONDS """""""""""""""""""""" #12
#3.2.1 ,ELECTRON ,DOTS """"""""" #12
#3.2.2 ,HORIZONTAL """"""""""""" #14
#3.2.3 ,OBLIQUE """""""""""""""" #15
#3.2.4 ,V]TICAL """""""""""""""" #16
#3.2.5 ,W$GES1 ,V]TICAL OR
,OBLIQUE """"""""""""""""""" #17
#3.2.6 ,W$GES1 ,HORIZONTAL """"" #18
#3.3 ,R+ ,/RUCTURES """""""""""""" #18
#3.4 ,MISCELLANE\S ,SYMBOLS &
,9DICATORS """"""""""""""""""" #19
#3.4.1 ,*EMICAL ,P]IOD """"""""" #19
#3.4.2 ,MODIFI]S """"""""""""""" #19
#3.4.3 ,L9ES """"""""""""""""""" #19
#3.4.4 ,MODIFI$-,LR ,9DICATORS #19
#3.5 ,SYMBOLS =! ,*EMICAL ,ELE;TS #20
#3.5.1 ,CAPITALIZ,N """""""""""" #20
#3.5.2 ,SPAC+ """""""""""""""""" #20
#3.5.3 ,PUNCTU,N """"""""""""""" #20
#4 ,,*EMICAL ,,=MULAS ,,& ,,EQU,NS #21
#4.1 ,*EMICAL ,=MULAS """""""""""" #21
#4.1.1 ,G5]AL ,=MULA """"""""""" #21
#4.1.2 ,EMPIRICAL ,=MULA """"""" #21
#4.1.3 ,MOLECUL> ,=MULA """""""" #21 #4.1.4 ,/RUCTURAL ,=MULA """"""" #21
#4.1.5 ,ELECTRON ,DOT ,=MULA """ #22
#4.2 ,>R[S """"""""""""""""""""""" #24
#4.2.1 ,HORIZONTAL ,>R[S """"""" #24
#4.2.2 ,V]TICAL ,>R[S """""""""" #26
#4.2.3 ,L1D ,L9ES & ,L1D ,>R[S #30
#4.2.4 ,DIPOLE ,>R[ """""""""""" #33
#4.2.5 ,MODIFIC,N ( ,>R[S """""" #33
#4.2.6 ,>R[ ,BONDS """"""""""""" #37
#4.3 ,ELECTRON ,DOT ,BONDS """"""" #40
#4.3.1 ,PLACE;T ( ,ELECTRON
,DOTS """""""""""""""""""""" #40
#4.3.2 ,PROPOR;N """"""""""""""" #44
#4.4 ,O!R ,BONDS """"""""""""""""" #45
#4.4.1 ,HORIZONTAL ,BONDS """""" #45
#4.4.2 ,V]TICAL ,BONDS """"""""" #46
#4.4.3 ,=MAT """"""""""""""""""" #46
,,VOLUME #2
#4.4.3 ,=MAT (3T9U$) ,,,,,,,,,,, #53
#4.5 ,MISCELLANE\S ,SYMBOLS """""" #71
#4.5.1 ,*EMICAL ,P]IOD """"""""" #71
#4.5.2 ,SEP>ATORS OR ,"PI;NS """ #71
#4.6 ,NEME? ,NOT,N 9 ,*EMICAL
P#E ,EQU,NS """""""""""""""""""""" #73
#4.7 ,FACTOR-,LABEL OR ,FRAC;N
,-PUT,N ,,,,,,,,,,,,,,,,,,,,,, #75
#4.7.1 ,=MAT """"""""""""""""""" #75
#4.7.2 ,RUNOV]S """""""""""""""" #75
#4.8 ,DIAGRAMS """"""""""""""""""" #78
#4.9 ,VOLTAIC (,ELECTRO*EMICAL OR
,GALVANIC ,CELL) ,NOT,N """""" #79
#5 ,,LABELS """""""""""""""""""""""" #81
#5.1 ,LABELS 6,*EMICAL ,EXPRES.NS #81
#5.2 ,REM>KS OR ,3DI;NS """""""""" #86
#5.3 ,LABEL$ ,,SYMBOLS & ,BONDS "" #87
#5.3.1 ,*A9S """"""""""""""""""" #87
#5.3.2 ,R+S """""""""""""""""""" #99
,,VOLUME #3
#6 ,,TYPE ,,=MS ,,9 ,,MA!MATICAL
,,EXPRES.NS """"""""""""""""" #109
#7 ,,SUP]SCRIPTS ,,& ,,SUBSCRIPTS #113
#7.1 ,SIMULTANE\S & ,NON-
SIMULTANE\S ,SUP]SCRIPTS &
,SUBSCRIPTS """"""""""""""""" #113
#7.2 ,ELECTRON ,*>GE """""""""""" #114
#7.3 ,ATOMIC ,NUMB]S & ,MASS
,NUMB]S """"""""""""""""""""" #116 #8 ,,"NS ,,( ,,*EMICAL ,,-P.DS """" #117
#8.1 ,PR9T ,=M """""""""""""""""" #117
#8.2 ,3TRAC;NS """""""""""""""""" #118
#8.3 ,DIVI.N ( ,"NS ( ,*EMICAL
,-P.DS """""""""""""""""""""" #119
#9 ,,A2REVI,NS ,,& ,,ACRONYMS """"" #121
#9.1 ,G5]AL ,RULES """""""""""""" #121
#9.2 ,PHYSICAL ,/ATES """"""""""" #123
#9.3 ,/&>D ,9T]N,NAL ,UNITS (
,M1SURE;T """"""""""""""""""" #123
#9.4 ,LRS ,REPRES5T+ ,*EMICAL
,GR\PS """""""""""""""""""""" #125
#9.5 ,LRS ,REPRES5T+ ,3C5TR,N (
,SOLU;NS """""""""""""""""""" #128
#9.6 ,ROMAN ,NUM]ALS ,FOLL[$ BY
,LRS """""""""""""""""""""""" #130
,,9DEX ,,( ,,BRL ,,SYMBOLS ,,=
,,*EMICAL ,,NOT,N """"""""""""" #131
,,9DEX """""""""""""""""""""""""""" #141
P#G
,,BRL ,,CODE ,,= ;I-;VII
,,*EMICAL ,,NOT,N
,,PREFACE
,? CODE IS BAS$ ON ! ..,NEME? ,BRL
,CODE = ,MA!MATICS & ,SCI;E ,NOT,N1
#1972 .,REVI.N4 ,S9CE ! ,NEME? ,CODE
DOES N 9CLUDE SYMBOLS & RULES = *EMI/RY
NOT,N1 TRANSCRIP;NS ( *EMICAL MAT]IAL H
V>I$ GRTLY DEP5D+ ON ! ID1S (! 9DIVIDUAL
TRANSCRIB]4 ,! ,MA!MATICS ,TE*NICAL
,-MITTEE (! ,BRL ,AU?OR;Y ( ,NOR? ,AM]I-
CA (,,BANA) FELT "! 0 A GRT NE$ = UNI=M-
;Y &! ,,BANA ,BO>D AGRE$4
,! ,,BANA ,MA!MATICS ,TE*NICAL ,-MIT-
TEE EXAM9$ *EMI/RY TEXTBOOKS & EXAMPLES
SUBMITT$ 0TRANSCRIB]S 6? -MITTEE & 6!
,N,NAL ,BRL ,ASSOCI,N ,MA!MATICS ,-MIT-
TEE = _M YE>S 6DECIDE ! 3T5T (A CODE4
,SYMBOLS = BONDS1 ELECTRON DOTS1 & O!R
SYMBOLS N 9CLUD$ 9 ! ,NEME? ,CODE 7 C>E-
;LLY SELECT$ & RULES = _! USE 7 =MULAT$4
,TRANSCRIB]S & R1D]S H BE5 9VOLV$ 9 ?
5D1VOR4 ,!Y H REVIEW$ ! CODE1 EVAL- #A UAT$ X1 & (F]$ -;TS & SU7ES;NS A;VII
6IMPROVE X4 ,^? :O H US$ X H F.D X E6EC-
TIVE4
,! ,,BANA ,MA!MATICS ,TE*NICAL ,-MIT-
TEE ?ANKS ALL :O H BE5 9VOLV$ 9 ? "W4
,SPECIAL ?ANKS >E EXT5D$ 6,PRISCILLA
,H>RIS & ,ROB9 ,BANK]1 :O H ASSI/$ 9 !
PRODUC;N ( ? DOCU;T4
,,BANA ,,MA!MATICS ,,TE*NICAL
,,-MITTEE
,VON ,EUL]T1 ,*AIR
,*RI/OPH] ,GRAY
,HEL5 ,MC,MILLAN
,JOYCE ,VAN ,TUYL
,JANE ,CORCORAN1 ,3SULTANT
,,9TRODUC;N ;VIII-;IX
,ANY SYMBOLS & RULES 9 ? ,CODE : DI6]
F ^? (! ..,NEME? ,CODE = ,MA!MATICS &
,SCI;E .,NOT,N >E 6BE US$ 9 *EMI/RY NO-
T,N EXCLUSIVELY & >E N 6BE US$ 9 ,NEME?
,CODE TRANSCRIP;NS4
,"S SPECIFIC 9/.ES ( DI6]+ RULES >E !
FOLL[+3
.,RUNOV] .SITES3 ,REG>D.S ( PR9T =MAT1
RUNOV] SITES ( L9KS 9 *EMICAL EQU,NS >E
9D5T$ TWO CELLS 6! "R (! SIGNS ( -P>I-
SON4 (,SEC;N #2)
.,C.ELL,N3 ,L9E> TRANSCRIP;NS ( UNCOM-
PLICAT$ FRAC;NS 3TA9+ C.ELL,N ) NO RE-
PLACE;T SYMBOLS >E =BI45 9 ! ,NEME?
,CODE B >E P]MITT$ 9 ? CODE4
.,CAPITALIZ,N .& .PUNCTU,N3 ,ALL LRS
9 ACRONYMS & A2REVI,NS M/ 2 CAPITALIZ$
9DIVIDU,Y & M/ 2 PUNCTUAT$ 9 ! MA!MAT-
ICAL MODE4 ,SPAC+ MAY AL DI6] F ! ,NEME?
,CODE4 (,SEC;N #9)
.,TRANSCRIB]'S .,NOTES .PAGE3 ,IF A
,NEME? ,CODE TRANSCRIP;N 3TA9S "S #C *EMI/RY NOT,N1 CITE ! USE ( ? A;IX
,*EMI/RY ,CODE1 AL;G ) XS DATE ( ADOP;N1
ON ! ,TRANSCRIB]'S ,NOTES PAGE4
.,SPECIAL .,SYMBOLS .PAGE4 ,A LI/ (
ANY *EMI/RY SYMBOLS US$ T >E N 9CLUD$ 9
! ,NEME? ,CODE M/ 2 LI/$ ON ! ,SPECIAL
,SYMBOLS PAGE4 ,^! SYMBOLS >E %[N 9
,SEC;N #1 (,BRL ,9DICATORS) & ,SEC;N #3
(,*EMICAL ,SIGNS & ,SYMBOLS)_4
,:5 ? ,*EMI/RY ,CODE DOES N A4RESS A
"PICUL> TRANSCRIB+ PRO#M1 ! RULES (!
,NEME? ,CODE %D 2 US$4 ,SEE ,EXAMPLE
#4.2.6-1 Z AN 9/.E ( S* A SITU,N4
#1 ,,BRL ,,9DICATORS4 ,9 A4I;N 6! #A
BRL 9DICATORS LI/$ 9 ,RULE ;,I ( ..,!
,NEME? ,BRL ,CODE = ,MA!MATICS & ,SCI;E
.,NOT,N1 ! FOLL[+ 9DICATORS >E PROVID$ =
*EMICAL NOT,N4
,HORIZONTAL ,BOND ,9DICATORS3
,OP5+ _
,CLOS+ ]
,RUNOV] ,LOCATOR #N (;N REPRES5TS AN
UPP] NUMB] ASSIGN$ 0! TRANSCRIB])
#1.1 ..,3/RUC;N (A ,HORIZONTAL
.,BOND4 ,! -PON5TS (A HORIZONTAL BOND >E
ASSEM#D 9 ! FOLL[+ ORD]3
(1) ,OP5+ ,9DICATOR
(2) ,HORIZONTAL ,BOND ,SYMBOL
(3) ,CLOS+ ,9DICATOR
,EXAMPLE #1.1-1_3 ,H_3],O_3],H
#1.2 .,RUNOV] .,LOCATOR4 ,RUNOV]
#1--#1.2 #E LOCATORS >E US$ ) SPATIAL /RUCTURES A#A
6ORI5T ! R1D] 6! PR9T >RANGE;T4 ,IF A
SPATIAL /RUCTURE M/ 2 RUN OV] &! RUNOV]
SITE IS N OBVI\S1 RUNOV] LOCATORS M/ 2
US$4 (,SEE ,EXAMPLES #4.4.3-6 &
#4.4.3-13_4)
,IF A /RUCTURE REQUIRES A RUNOV]
LOCATOR = ORI5T,N ( RUNOV] SITES1 ! RUN-
OV] LOCATOR & XS ASSOCIAT$ NUMB] M/ 2
9S]T$ AF ! LA/ SYMBOL AT ! RUNOV] SITE4
,! F/ RUNOV] SITE IS LABEL$ #A1 ! SECOND
#B1 ETC4 ,ID5TICAL LOCATORS >E !N 9S]T$
2F ! F/ SYMBOL (! 3T9U$ L9E(S)_4
,9 A BRAN*$ /RUCTURE ": 9DIVIDUAL
BRAN*ES REQUIRE RUNOV]S1 NUMB] ! RUNOV]
SITES ( EA* BRAN* 9 SEQU;E4 (,SEE ,EXAM-
PLE #4.2.5-2_4)
#1.3 .,SPAC+4 ,ALL 9DICATORS &
LOCATORS M/ 2 UNSPAC$ F ! MAT]IAL 6: !Y
APPLY4
--------------------------------------#B
#1.4 .,PUNCTU,N4 ,9DICATORS M/ 2
PUNCTUAT$ 9 ! MA!MATICAL MODE4 (,SEE
@,S#37, ,NEME? ,CODE4)
,EXAMPLE #1.4-1_3 A#B
,IF Y REMOVE "O HYDROG5 ATOM F ME?ANE1
,C,H4, ! RESULT IS ! ME?YL RADICAL1
,C,H3_3]_4
#1.2--#1.4-1 #G
#2 ,,G5]AL ,,=MAT #C
#2.1 .,RUNOV] .,SITES4 ,RUNOV] SITES
M/ 2 SELECT$ C>E;LLY 6M9IMIZE ! NUMB] (
RUNOV]S & 6KEEP RELAT$ MAT]IAL 9TACT4 ,D
N DIVIDE ANY MA!MATICAL EXPRES.N IF X C
2 3TA9$ ON "O L9E4 ,AVOID RUNN+ OV] )9
MAT]IAL 2T BONDS1 R+ /RUCTURES1 SUP]-
SCRIPTS OR SUBSCRIPTS1 & MODIFIC,NS4
#2.2 ..,PREF];E ,LI/ = .,RUNOV]S4
,:5 A *EMICAL EXPRES.N _C 2 KEPT ON "O
BRL L9E & M/ 2 DIVID$ 2T L9ES1 ! DIVI.N
M/ 2 MADE GIV+ PRIOR;Y 6! FOLL[+ ITEMS 9
DESC5D+ ORD]3
(1) ,2F A SYMBOL ( -P>ISON
(2) ,2F A SYMBOL ( OP],N
(3) ,2F AN OP5+ FRAC;N 9DICATOR
(4) ,2F A *EMICAL BOND
(5) ,2F A FRAC;N L9E
(6) ,2F ! BASE-L9E 9DICATOR @#
(7) ,2F A *ANGE-(-LEVEL 9DICATOR OR )9 A
SUP]SCRIPT OR SUBSCRIPT 2F "O (!
SYMBOLS LI/$ ABV
(8) ,AF A -MA : O3URS 2T ITEMS 9 AN
#2--#2.2 #I 5CLOS$ LI/ A#C
(9) ,2T FACTORS : >E 5CLOS$ )9 GR\P+
SYMBOLS
(10) ,AF A T]M9,N 9DICATOR4
@# ,! BASEL9E 9DICATOR ASSUMES !
PRIOR;Y POSI;N (! SYMBOL : FOLL[S X4
(,SEE EXAMPLES #6.8 & #7.1.2_4)
,FRAC;NS1 P>5!TICAL EXPRES.NS1 & *EM-
ICAL =MULAS %D 2 -PLET$ ON "O BRL L9E IF
POSSI#4 ,IF ! NUM]ATOR OR DENOM9ATOR (A
FRAC;N M/ 2 RUN OV]1 A DIVI.N M/ O3UR AL
AT ! FRAC;N L9E4 ,IF A *EMICAL -P.D 9 A
MA!MATICAL L9K M/ 2 RUN OV]1 A DIVI.N M/
2 MADE AL AT A SIGN ( OP],N (,SEE EXAM-
PLE #2.5-2_4)
#2.3 .,L9K$ .,EXPRES.NS4 ,IF A DIS-
PLAY$ EXPRES.N IS TOO L;G 6FIT ON "O L9E
& 3TA9S 8L9KS0 (AS DEF9$ 9 @,S#189 (!
,NEME? ,CODE), ! SPECIAL M>G9 REQUIRE;TS
= L9K$ EXPRES.NS (! ,NEME? ,CODE
(@,S#190C, @,S#191A(IV) & B(V)) APPLY
REG>D.S (! PR9T =MAT4 ,?US3
(1) ,9D5T TWO CELLS F ! AN*OR M>G9 :5 !
RUNOV] 2G9S )A -P>ISON SYMBOL4 (2) ,:5 ! RUNOV] 2G9S ) "S SYMBOL B#C
O!R ?AN A -P>ISON SYMBOL1 9D5T F\R
CELLS 6! "R (! AN*OR M>G94 (,SEE
,EXAMPLE #2.5-2 2L4)
--------------------------------------#D
(3) ,:5 REM>KS1 3DI;NS1 OR EXPLAN,NS
APPE> )! =MULA1 />T !M ON A NEW L9E &
BLOCK ? MAT]IAL #6 CELLS 6! "R (!
AN*OR M>G94
#2.4 ..,4PLAY$ ,EXPRES.NS ,3TA9+ ,NO
,L9KS4 ,IF S* AN EXPRES.N M/ 2 RUN OV]
6A NEW L9E OR L9ES1 ! SECOND & SU3E$+
L9ES M/ 2 9D5T$ TWO CELLS 6! "R (! 2G9N+
(! EXPRES.N4
#2.5 ..,RUNOV]S ( ,L9E> & ,SPATIAL
,=MULAS4 ,IF A L9E> =MULA IS RUN OV] 6A
NEW L9E OR L9ES1 NO RUNOV] LOCATORS >E
US$ Z ! LOC,N (! 3T9U$ L9E IS OBVI\S4 ,9
A4I;N1 IF A SIMPLE SPATIAL =MULA IS RUN
OV] 6A NEW L9E &! RUNOV] SITE IS OBVI\S1
NO RUNOV] LOCATOR IS NEC4
,EXAMPLE #2.5-1_3 (,L9E> ) RUNOV] 2F
#2.3--#2.5-1 #AA -P>ISON SYMBOL) A#D
,CA,C2+2,H,O,H
$O ,H_3],C_=],C_3],H+,CA(,O,H);2
,EXAMPLE #2.5-2_3 (L9E> ) MULTIPLE
RUNOV]S)
,C,H3(,C,H2);10",C,H2,O,S,O2,O,H
+,NA^+",O,H^-
$O ,C,H3(,C,H2);10",C,H2,O,S,O2,O^-
",NA^+
"+,H2,O
,EXAMPLE #2.5-3_3 (SIMPLE SPATIAL
/RUCTURE1 NO -P>ISON SYMBOLS)
,C,H3
_
,C,H3_3],C,H_3],C,H2_3],C,H2_3],C,H2
_3],C,H3
--------------------------------------#E
,EXAMPLE #2.5-4_3 (SPATIAL /RUCTURE
REQUIR+ A RUNOV] LOCATOR) [O ,N A#E
_// _* _/ _**
[O [O _**
_ __ [O#A
[O [O _/
_/ _** _/ _* _/
,H,O [O ,S
,N
_// _*
_// _* ,H
_// _* _1/
_// [O
_// _ _V
_// _ ,C_3],O_3],R
#A_3][O _ __
_* _ ,O
_* _
_* _ ,H
_* _ _1/
_* [O
_* _/ _V
_* _/ ,H
,S
#2.5-1--#2.5-4 #AC #2.6 .,SPATIAL .,MAT]IAL4 #F
,/RUCTURES O3UPY+ M ?AN "O PR9T L9E &
HAV+ A V]TICAL REL,N%IP >E SPATIAL
>RANGE;TS4 ,9 BRL1 SPATIAL MAT]IAL M/ 2
PREC$$ & FOLL[$ 0A BLANK L9E4
.,EMB$D$4 ,:5 SPATIAL EXPRES.NS >E
EMB$D$ 9 N>RATIVE TEXT1 ! POR;NS (
N>RATIVE TEXT : O3UR ON ! SAME BRL L9E Z
! SPATIAL /RUCTURE M/ 2 ALIGN$ )! MA9
L9E (! /RUCTURE4
.,4PLAY$4 ,9 4PLAY$ SPATIAL EXPRES.NS1
! LEFTMO/ SYMBOL M/ 2G9 #2 CELLS 6! "R (
! CURR5T M>G94 ,,EXCEP;N3 ,X IS P]MISSI#
6/>T A /RUCTURE T O3UPIES M* SPACE BO?
HORIZONT,Y & V]TIC,Y (E4G41 A R+
/RUCTURE OR A SPATIAL /RUCTURE (A V L>GE
MOLECULE), 9 CELL #1 9 ORD] 6AVOID A
RUNOV]4 (,SEE ,EXAMPLE #4.4.3-21_4) ,?
EXCEP;N %D 2 US$ SP>+LY4
.,ID5TIFI$4 ,:5 A SPATIAL /RUCTURE OR
EXPRES.N IS ID5TIFI$ 0A NUMB] OR LR (AS
9 AN EXAMPLE OR SET ( EX]CISES), !
ID5TIFI] M/ 2 PLAC$ AT ! TOP L9E (!
/RUCTURE 9 BRL4 ,"O COLUMN ( BLANK CELLS
M/ 2 LEFT 2T ! ID5TIFI] &! LEFT-MO/ SYMBOL (! /RUCTURE4 ,IF 0PLAC+ ! A#F
ID5TIFI] ON A SEP>ATE L9E X IS POSSI# TO
GET ! -PLETE /RUCTURE ACR ! PAGE1 ? MAY
2 D"O4 ,A BLANK L9E M/ 2 LEFT 2T !
ID5TIFI] &! SPATIAL /RUCTURE4
.,*EMICAL .,EQU,NS4 ,:5 A *EMICAL
EQU,N 3SI/S (A SPATIAL ELE;T &A L9E>
ELE;T SEP>AT$ 0A SIGN ( OP],N (USU,Y A
PLUS SIGN), ! L9E> ELE;T1 AL;G )! SIGN (
OP],N M/ 2 PLAC$ S T ..X IS N 9 DIRECT
.3TACT ) ANY BRAN* (! SPATIAL /RUCTURE
EI .V]TIC,Y .OR .DIAGON,Y4 ,A CLE> BLANK
CELL M/ 2 LEFT 2T ! 2G9N+ (OR 5D) (!
L9E> ELE;T &A V]TICAL OR DIAGONAL BRAN*
(! SPATIAL /RUCTURE 6PREV5T DIRECT
3TACT4 (,SEE ,EXAMPLE #4.2.3-4_4)
,MOREOV]1 A DIAGONAL POR;N (! SPATIAL
/RUCTURE MAY N 8OV]LAP0 ! L9E> ELE;T EI
ABV OR 2L EV5 IF ? CD 2 D"O )\T MAK+
DIRECT 3TACT4 ,H["E NO CLE> BLANK CELL
IS NEC IF ! PLACE;T (! L9E> POR;N DOES N
MAKE DIRECT V]TICAL OR DIAGONAL 3TACT )A
BRAN* (! SPATIAL /RUCTURE4 (,SEE
,EXAMPLES #4.2.5-2, #4.8-2_4)
#2.6 #AE ,A L9E> ELE;T .MAY 2 PLAC$ ADJA- B#F
C5T 6A R+ /RUCTURE OR 6A HORIZONTAL POR-
;N (A SPATIAL /RUCTURE IF T IS ! PR9T =-
MAT & IF ! L9E> POR;N C 2 BRLD S T NO "P
( X IS 9 DIRECT 3TACT )A V]TICAL OR DI-
AGONAL BRAN* (! SPATIAL /RUCTURE4 (,SEE
,EXAMPLE #4.2.6-3_4)
,IF X IS NEC 6PLACE A L9E> POR;N ( AN
EQU,N S F> 4TANT F ! MA9 L9E (A SPATIAL
/RUCTURE T X IS DI6ICULT 6LOCATE1 !
5L>G$ TRANSCRIB]'S GR\P+ SYMBOLS MAY 2
US$ &! L9E> MAT]IAL TOP-ADJU/$ 6! GR\P+
SYMBOLS4 (,SEE ,EXAMPLE #2.6-4_4)
,EXAMPLE #2.6-1_3 (EMB$D$ SPATIAL #G
EXPRES.N)
N 3TRIBUTE EQU,Y4 ,! HYBRID IS E/IMAT$
?
6BE #10 P]C5T ^+"?,C?,O?^-, #20 P]C5T
?
EA* ?,C??,O? & ?,C??,O?, & #50 P]C5T
?
^-"?,C\,O?^+_4 ,! ELECTRONEGATIV;Y ,,,
,EXAMPLE #2.6-2_3 (4PLAY$ SPATIAL
EXPRES.N)
--------------------------------------#H
,T = AN ATOM ( *LOR9E IS
?
*,CL?
?
#2.6--#2.6-2 #AG ,:5 ^! ATOMS REACT1 SODIUM ATOMS A#H
2COME SODIUM IONS4 ,! ELECTRON-DOT
SYMBOL =A SODIUM ION IS
,NA^+
,! *LOR9E ATOMS 2COME *LORIDE IONS1 : H
! ELECTRON-DOT SYMBOL
?
],CL?^-
?
,^! IONS =M ! -P.D SODIUM *LORIDE4 ,!
ELECTRON DOT =MULA = SODIUM *LORIDE MAY
2 WRITT5 Z
?
,NA^+"],CL?^-
?
OR Z A SIMPL] IONIC =MULA1 ,NA^+",CL^-_4
,EXAMPLE #2.6-3_3 (L9E> ADJAC5T #I
6SPATIAL)
,C,H3
_*
,H,O^-"+ ,C_3],I
_;/ _V
,H ,H
,C,H3
_
$O ,O_1],C_1],I
_/ _2/ _V
,H ,H ,H
,H_3],O
_*
$O ,C_3],C,H3+,I^-
_2/ _V
,H ,H
#2.6-2--#2.6-3 #AI ,EXAMPLE #2.6-4_3 (REQUIRES A#I
TRANSCRIB]'S GR\P+ SYMBOLS2 :AT APPE>S
Z A BOLD DOT IS A NORMAL ELECTRON DOT
9 ? TEXT)
[ ,')^-
[,O[ ,')
[ # [ ,')
[,O#,N:,O>,')
[ [ ,')
-------------------------------------#AJ
#2.7 .,C.ELL,N4 ,MAT]IAL 3TA9+
C.ELL,N ) NO REPLACE;T SYMBOLS MAY 2
TRANSCRIB$ L9E>LY4 (,NEME? ,CODE ,RULE
,,XI REQUIR+ SPATIAL >RANGE;T DOES N
APPLY 9 ? SITU,N4) (SEE ,EXAMPLE
#9.5-6_4)
#3 ,,*EMICAL ,,SIGNS ,,& ,,SYM- #AA
BOLS
#3.1 .,*EMICAL .,>R[S4 ,! BRL
REPRES5T,N ( >R[S LI/$ 2L M/ 2 US$ 9
PLACE (! "OS LI/$ 9 ! ,NEME? ,CODE4 ,ALL
O!R >R[S M/ 2 TRANSCRIB$ Z REQUIR$ 0!
,NEME? ,CODE4
,UP-PO9T+
,REGUL> """""""""""""""""" $<
,BOLDFACE """""""""""""""" $_<
,D[N-PO9T+
,REGUL> """""""""""""""""" $%
,BOLDFACE """""""""""""""" $_%
,BOLD UP-PO9T+ FOLL[$
0,REGUL> D[N-PO9T+ """"""" $_<"%
,REGUL> UP-PO9T+ FOLL[$
0BOLD D[N-PO9T+ """""""""" $<"_%
,REGUL> UP-PO9T+ FOLL[$
0REGUL> D[N-PO9T+ """""""" $<"%
,V]TICAL OR OBLIQUE DIPOLE
,UP-PO9T+ """""""""""""""" $+<
,D[N-PO9T+ """"""""""""""" $+%
#2.6-4--#3.1 #BA ,HALF-B>B UP-PO9T+ FOLL[$ A#AA
0HALF-B>B D[N-PO9T+ """""" $@<",%
-------------------------------------#AB
,HORIZONTAL
,DIPOLE1 "R-PO9T+ """""""" $+3O
,DIPOLE1 LEFT-PO9T+ """""" $[3+
,CROSS$ >R[ """""""""""""" /$[3O
#3.2 .,BONDS
#3.2.1 .,ELECTRON .,DOTS
,S+LE REGUL> """"""""""""""""""" *
,S+LE BOLD OR HOLL[ """""""""""" /
,SMALL ;X """""""""""""""""""""" X
,PAIR1 REGUL> """""""""""""""""" ?
,PAIR1 HOLL[ OR BOLD """"""""""" #
,PAIR1 ;X_'S """"""""""""""""""" [
,PAIR1 "R OR UPP] BOLD OR H[LL[1
LEFT OR L[] REGUL> """"""""""" ]
,PAIR1 "R OR UPP] ;X, LEFT OR
L[] REGUL> """"""""""""""""""" %
,PAIR1 "R OR UPP] REGUL>" LEFT
OR L[] BOLD OR HOLL[ """"""""" &
-------------------------------------#AC
,PAIR1 "R OR UPP] REGUL>1 LEFT
OR L[] ;X """""""""""""""""""" $ ,PAIR1 "R OR UPP] BOLD OR HOLL[1 A#AC
LEFT OR L[] ;X """"""""""""""" :
,PAIR1 "R OR UPP] ;X, BEFT OR
L[] BOLD OR HOLL[ """""""""""" >
,TRIPLET (?REE PAIRS ( REGUL>
ELECTRON DOTS) """"""""""""""" \
,O!R TRIPLETS
,9S]T DOTS #46 2F A PAIR %[N
HORIZONT,Y 9 ! LI/ ABV 69DICATE
T ! >RANGE;T IS A TRIPLET4 ,=
EXAMPLE 1111111111111111111111 .%
,'#3 V]TICAL REGUL> DOTS
FOLL[$ BY #3 V]TICAL ;X_'S,'
-------------------------------------#AD
#3.2.2 .,HORIZONTAL
(9CLUD+ 9DICATORS)
,S+LE """"""""""""""""""""""" _3]
,D\# """""""""""""""""""""""" _7]
,TRIPLE """"""""""""""""""""" _=]
,>R[1 "R-PO9T+ """""""""""""" _3O]
,>R[1 LEFT-PO9T+ """""""""""" _[3]
,B>R$ """"""""""""""""""""""" _\]
,BOLD """"""""""""""""""""""" _G]
,BROK5 """""""""""""""""""""" _2]
#3.2--#3.2.2 #BC ,DOTT$ """""""""""""""""""""" _1] A#AD
,JA7$1 S+LE """"""""""""""""" _E]
,JA7$1 D\# """""""""""""""""" _EI]
,WAVY1 S+LE """"""""""""""""" _9]
,WAVY1 D\# """""""""""""""""" _95]
-------------------------------------#AE
#3.2.3 .,OBLIQUE
,L[] LEFT 6UPP] "R """"""""""" _/
,L[] LEFT 6UPP] "R1 D\# """""" _//
,UPP] LEFT 6L[] "R """"""""""" _*
,UPP] LEFT 6L[] "R1 D\# """""" _**
,>R[1 L[] LEFT 6UPP] "R """""" _/<
,>R[1 L[] "R 6UPP] LEFT """""" _*<
,>R[1 UPP] LEFT 6L[] "R """""" _*%
,>R[1 UPP] "R 6L[] LEFT """""" _/%
,BROK51 L[] LEFT 6UPP] "R """" _2/
,BROK51 UPP] LEFT 6L[] "R """" _2*
,DOTT$1 L[] LEFT 6UPP] "R """" _1/
,DOTT$1 UPP] LEFT 6L[] "R """" _1*
,B>R$, L[] LEFT 6UPP] "R """"" _X/
,B>R$1 UPP] LEFT 6L[] "R """"" _X*
#3.2.4 ,V]TICAL #AF
,S+LE """""""""""""""""""""""" _
,D\# """"""""""""""""""""""""" __
,TRIPLE """""""""""""""""""""" ___
,>R[1 UP-PO9T+ """"""""""""""" _<
,>R[1 D[N-PO9T+ """""""""""""" _%
,B>R$ """""""""""""""""""""""" _X
,BOLD """""""""""""""""""""""" _G
,BROK5 """"""""""""""""""""""" _2
,DOTT$ """"""""""""""""""""""" _1
,JA7$1 S+LE """""""""""""""""" _E
,JA7$1 D\# """"""""""""""""""" _EI
,WAVY1 S+LE """""""""""""""""" _9
,WAVY1 D\# """"""""""""""""""" _95
#3.2.3--#3.2.4 #BE #3.2.5 ..,W$GES1 ,V]TICAL OR #AG
.,OBLIQUE
,D[N-PO9T+1 NORMAL \TL9E """"" _M
,UP-PO9T+1 NORMAL \TL3E """""" _U
,D[N-PO9T+1 FILL$ 9 """""""""" _P
,UP-PO9T+1 FILL$ 9 """"""""""" _V
,D[N-PO9T+1 DOTT$ \TL9E """""" _1M
,UP-PO9T+1 DOTT$ \TL9E """"""" _1U
,D[N-PO9T+1 DA%$ \TL9E """"""" _2M
,UP-PO9T+1 DA%$ \TL9E """""""" _2U
,D[N-PO9T+1 B>R$ """"""""""""" _XM
,UP-PO9T+1 B>R$ """""""""""""" _XU
-------------------------------------#AH
#3.2.6 .,W$GES1 .,HORIZONTAL
(9CLUD+ 9DICATORS)
,"R-PO9T+1 NORMAL \TL9E """""" _O]
,LEFT-PO9T+1 NORMAL \TL9E """" _[]
,"R-PO9T+1 FILL$ 9 """"""""""" _R]
,LEFT-PO9T+1 FILL$ 9 """"""""" _W]
,"R-PO9T+1 DOTT$ \TL9E """"""" _1O]
,LEFT-PO9T+1 DOTT$ \TL9E """"" _1[]
,"R-PO9T+1 DA%$ \TL9E """""""" _2O]
,LEFT-PO9T+1 DA%$ \TL9E """""" _2[]
,"R-PO9T+1 B>R$ """""""""""""" _\O]
,LEFT-PO9T+1 A#AH
B>R$ """"""""""""""""""""" _\[]
#3.3 .,R+ .,/RUCTURES
,V]TICES (? TWO-CELL$ SYMBOL
REPRES5TS .ANY .UNLABEL$
V]TEX) """"""""""""""""""""""" [O
,CIRCLE1 (BROK5 \TL9E) """"""""" $BC
,HEXAGON (BROK5 \TL9E) """"""""" $B6
-------------------------------------#AI
#3.4 ..,MISCELLANE\S ,SYMBOLS &
.,9DICATORS
#3.4.1 .,*EMICAL .,P]IOD *
#3.4.2 .,MODIFI]S3 ,^! SYMBOLS >E
6BE US$ Z SPATIAL MODIFI]S ONLY4 ,9 L9E>
EXPRES.NS1 ! FULL 3/RUCT (! ,NEME? ,CODE
M/ 2 US$4 (,SEE ,EXAMPLES #5.3.1-9 &
#7.2-3_4)
,CROSS$ ;,O """""""""""""""""""" @.O
,PLUS SIGN )9 A CIRCLE """1""""" $C+
,M9US SIGN )9 A CIRCLE 1"""""""" $C-
#3.2.5--#3.4.2 #BG #3.4.3 .,L9ES ("PI;NS1 N A#AI
BONDS)
,BROK5 V]TICAL """""""""""""""""" .\
,DOTT$ V]TICAL """""""""""""""""" @\
,DOTT$1 D\# V]TICAL """"""""""""" @\@\
,JA7$1 V]TICAL """""""""""""""""" @@\
,JA7$1 HORIZONTAL """"""""""""""" "5959
#3.4.4 .,MODIFI$-,LR .,9DICATORS
,SMALL ,CAPITAL @# """""""""""""" @",
,B>R$ ,CAPITAL """""""""""""""""" @;\,
@# ,ASSUM+ ! SMALL CAPITAL LR
IS ON ! SAME LEVEL Z NORMAL LRS4
,EXAMPLE #3.4.4-1 (SMALL CAPTIAL ;,D)
@",D
,EXAMPLE #3.4.4-2_3 (B>R$ CAPITAL ;,R)
@;\,R
-------------------------------------#BJ
#3.5 ..,SYMBOLS =! ,*EMICAL
.,ELE;TS4 ,! ,NEME? ,CODE DEF9ES 8SIGN0
Z ! PR9T$ M>K & 8SYMBOL0 Z ! BRL REPRE-
S5T,N ( T SIGN4 ,! USUAL NOM5CLATURE =! LR(S) REPRES5T+ ! "N (A *EMICAL A#BJ
ELE;T IS 8*EMICAL SYMBOL40 ,9 ? ,*EMI/RY
,CODE ! ^W 8,,SYMBOL0 (ALL UPP] CASE) IS
US$ 6DENOTE ! LR(S) REPRES5T+ A *EMICAL
ELE;T & 8SYMBOL0 (L[] CASE) 6DENOTE !
M1N+ Z GIV5 9 ! ,NEME? ,CODE4 ,A
,,SYMBOL =A *EMICAL ELE;T 3SI/S (A S+LE
CAPITALIZ$ LR OR A CAPITALIZ$ LR FOLL[$
0"O OR M L[] CASE LRS4 ,^! ,,SYMBOLS >E
N A2REVI,NS Z DEF9$ 0! ,NEME? ,CODE1
(I4E41 ,NEME? ,CODE ,RULE ,,VIII DOES N
APPLY 6,,SYMBOLS)_4
@#@# ,,CAU;N @#@# ,9 ,PR9T1
SANS]IF TYPE =M IS (T5 EMPLOY$ 9
TA#S & DIAGRAMS4 ,9 ? CASE1 ! CAPI-
TAL ;,I &! L[] CASE ;L >E EASILY
3FUS$4 ,^U C>E;L EXAM9,N X IS USU,Y
POSSI# 64T+UI% 2T !M Z ! ;,I IS
USU,Y ?ICK] ?AN ! ;L_4 ,2 AW>E ( ?
& 2 SURE 64CRIM9ATE4
#3.5.1 .,CAPITALIZ,N4 ,:5 ,,SYM-
BOLS APPE> 9 A S]IES1 Z 9 A MOLECULE1
EA* ,,SYMBOL M/ 2 CAPITALIZ$ 9DIVIDU,Y4
#3.4.3--#3.5.1 #BI #3.5.2 .,SPAC+4 ,FOLL[ ! B#BJ
PR9T SPAC+4
,EXAMPLE #3.5.2-1_3 ,C,H
,EXAMPLE #3.5.2-2_3 ,MG,O
,EXAMPLE #3.5.2-3_3 ,H_3],O_3],H
#3.5.3 .,PUNCTU,N3 ,*EMICAL
,,SYMBOLS M/ 2 PUNCTUAT$ 9 ! MA!MATICAL
MODE Z DEF9$ 9 ,NEME? ,CODE ,RULE ,,VI_4
,EXAMPLE #3.5.3-1_3 ,WAT] IS ,H,O,H_4
#4 ,,*EMICAL ,,=MULAS ,,& #BA
,,EQU,NS4 ,*EMICAL =MULAS & EQU,NS MAY
3TA9 ELECTRON DOTS1 BONDS1 MA!MATICAL
OP],N & -P>ISON SIGNS1 *EMICAL >R[S1 &
O!R NOT,N4
#4.1 ,*EMICAL ,=MULAS
#4.1.1 .,G5]AL .,=MULA4 ,AN EX-
PRES.N (! -POSI;N (A -P.D (OR RADICAL1
ETC4) 0A -B9,N ( ,,SYMBOLS & NUM]ALS 6%[
! 3/ITU5TS1 USU,Y 9 EXACT PROPOR;N4 ,!
FOLL[+ >E DEF9I;NS (! DI6]5T TYPES (
=MULAS4
#4.1.2 .,EMPIRICAL .,=MULA4 ,A
*EMICAL =MULA : GIVES ! -POSI;N (A -P.D
B DOES N SPECIFY ! /RUCTURAL >RANGE;T OR
PROPOR;N4
,EXAMPLE #4.1.2-1_2 (EMPIRICAL =MULA =
B5Z5E) ,C,H
#4.1.3 .,MOLECUL> .,=MULA4 ,A =MU-
LA : GIVES ! K9DS ( ATOMS OR RADICALS &!
NUMB] ( EA* K9D 9 A MOLECUL> -P.D4
#3.5.2--#4.1.3 #CA ,EXAMPLE #4.1.3-1_3 (MOLECUL> A#BA
=MULA = B5Z5E) ,C6,H6
#4.1.4 .,/RUCTURAL .,=MULA4 ,A =M-
ULA : ILLU/RATES ! >RANGE;T ( ATOMS &
BONDS 9 A MOLECULE4 ,/RUCTURAL =MULAS >E
SPATIAL >RANGE;TS & MAY 3TA9 8CLOS$
FIGURES10 CALL$ 8CYCLICAL0 OR 8R+0
/RUCTURES4
-------------------------------------#BB
,EXAMPLE #4.1.4-1_3 (B5Z5E R+)
,H
_
,C
_// _*
,H_3],C ,C_3],H
_ __
,H_3],C ,C_3],H
_** _/
,C
_
,H
#4.1.5 .,ELECTRON .,DOT A#BB
.,=MULA (AL "KN Z ,LEWIS ,ELECTRON ,DOT
,DIAGRAM)_4 ,? IS A =MULA : EMPLOYS !
,,SYMBOL ( AN ELE;T 6REPRES5T ! NUCLEUS
( AN ATOM & ALL ELECTRONS EXCEPT ^? 9 !
\T] LEVEL4 ,DOTS REPRES5T ! \T] LEVEL (
ELECTRONS1 DRAWN ON ! APPROPRIATE SIDES
(TOP1 BOTTOM1 LEFT1 "R) OR ON ! DIAGONAL
(UPP] LEFT1 UPP] "R1 L[] LEFT1 L[] "R)
(! ,,SYMBOL4
,EXAMPLE #4.1.5-1_3
,! 5]GY LEVELS & ORBITALS ( ,CD >E3
,CD
.K #1S^2"2S^2"2P^6"3S^2"3P^6"4S^2
"3D^10"4P^6"5S^2"4D^10
,\T] ELECTRONS .K #5S^2
,DOT FORMULA .K ,CD?
#4.1.4-1--#4.1.5-1 #CC ,EXAMPLE #4.1.5-2_3 (/RUCTURAL #BC
DIAGRAM 3SI/+ (A -B9,N ( MOLECUL>
BONDS & ELECTRON DOTS)
? ?
,F
? ?
_/ _1*
,H ,H
_1/ _*
? ? ? ?
,F ,F
? ? ? ?
_ _1*
,H ,H
_1* _
? ? ? ?
,F ,F
? ? ? ?
_* _1*
,H ,H
_1* _/
? ?
,F
? ? #4.2 .,>R[S4 ,! *EMICAL >R[S #BD
LI/$ 9 ,SEC;N #3.1 >E = USE 9 TRANSCRIB+
*EMICAL =MULAS ONLY4 ,V>I\S =MS ( >R[S
>E (T5 9CLUD$ 9 ^! =MULAS4 ,X IS
IMP]ATIVE T ! PR9T =M (! >R[S 2
REPRES5T$ 9 BRL4 ,IF D\# >R[ -B9,NS %[
"O >R[ H1VI] OR L;G] ?AN ! O!R1 ! DI6];E
IS SIGNIFICANT & ?US M/ 2 DUPLICAT$ 9
BRL4
#4.2.1 .,HORIZONTAL .,>R[S4 ,!
SYMBOLS = HORIZONTAL >R[S >E ^? LI/$ 9 !
,NEME? ,CODE4 ,A4$ 6? LI/ >E !
HORIZONTAL DIPOLES ($+3O & $[3+)_4
,EXCEPT = DIPOLES & >R[ BONDS1
HORIZONTAL >R[S >E SIGNS ( -P>ISON & >E
SPAC$ & PUNCTUAT$ 9 -PLI.E )! ,NEME?
,CODE1 ,RULE ,,XX_4
,EXAMPLE #4.2.1-1_3 (S+LE1 "R-PO9T+ >R[1
NORMAL B>B)
,CA3(,P,O4);2"+2,H2,S,O4
$O ,CA(,H2,P,O4);2"+2,CA,S,O4
#4.1.5-2--#4.2.1-1 #CE ,EXAMPLE #4.2.1-2_3 (D\# >R[S1 A#BD
EQUAL L5G?S1 NORMAL B>BS)
,H2(G)+,I2(G) $3O$[3 #2,H,I(G)
,EXAMPLE #4.2.1-3_3 (D\# >R[S1 EQUAL
L5G?S1 HALF-B>BS)
,O
__
,C,H3,C,H+,O,H
,O
__
$33@O$,[33 ,C,H2_3],C,H+,H2,O
-------------------------------------#BE
,EXAMPLE #4.2.1-4_3 (RESON.E &
EQUILIBRAT+ >R[S)
,9 RESON.E LANGUAGE1 WE MAY A#BE
DEPICT B5Z5E 0TWO EQUIVAL5T RESON.E
/RUCTURES4
@,( [O [O @,)
@,( _/ _** _// _* @,)
@,([O [O [O [O@,)
@,(__ _ $[33O _ __@,)
@,([O [O [O [O@,)
@,( _* _// _** _/ @,)
@,( [O [O @,)
,NOTE ! IMPORTANT DI6];E ''' ( NUCLEI4
[O [O
_// _* _/ _**
[O _* _/ [O
_ [O [O _
_ __ $33@O$,[33 __ _
_ [O [O _
[O _/ _* [O
_** _/ _* _//
[O [O
#4.2.1-2--#4.2.1-4 #CG ,EXAMPLE #4.2.1-5_3 (D\# >R[S1 #BF
DI6]5T L5G?S1 NORMAL B>BS)
,O_3],H ,O
_ __
[O [O ,H
_/ _** _/ _* _/
[O [O [O [O
__ _ $[33$3O __ _ _*
[O [O [O [O ,H
_* _// _* _//
[O [O
,EXAMPLE #4.2.1-6_3 (D\# >R[S1 UPP]
BOLD1 NORMAL B>BS)
,AG,N,O3 $_33O$[33 ,AG^+"+,N,O3"^-
#4.2.2 .,V]TICAL .,>R[S4 ,SEE !
,SYMBOLS ,LI/1 ,SEC;N #3 ( ? ,CODE4
,V]TICAL & OBLIQUE >R[S >E (T5 US$ TO
FACILITATE ! PRES5T,N (A #3-DIM5.NAL
FIGURE ON A #2-DIM5.NAL PAGE4 ,! FACT T
^! >E N HORIZONTAL (T5 HAS NO *EMICAL
SIGNIFIC.E4 ,X IS PREF]A# 6USE "R- & LEFT-PO9T+ >R[S IF ? W MAKE ! A#BF
PRES5T,N EASI] 6FOLL[ 9 BRL4 ,NORM,Y1
*EMICAL EQU,NS >E >RANG$ 9 PR9T F LEFT
6"R & F TOP 6BOTTOM4 ..,! DIREC;N (!
.REAC;N F "O -PON5T 6ANO!R M/ 2 PRES]V$4
,! >R[ DOES N M1N T ! REAC;N PROCE$S F !
"PICUL> ELE;T : PREC$ES ! >R[ B F !
5TIRE 3/RUCT4 (,SEE ,EXAMPLE #4.2.2-5_4)
,AL? UP-PO9T+ & D[N-PO9T+ >R[S >E
NORM,Y -P>ISON SIGNS1 9 A SPATIAL
>RANGE;T !Y O3UPY A L9E 0!MVS & NO BLANK
L9ES >E LEFT ABV OR 2L UN.S REQUIR$ 0O!R
3SID],NS4 .,NOTE3 ,UP-PO9T >R[S REPRE-
S5T+ VAPORIZ,N & D[N-PO9T+ >R[S REPRE-
S5T+ PRECIPIT,N >E N -P>ISON SIGNS4 ,S*
>R[S M/ 2 TRANSCRIB$ UNSPAC$ F ! ,,SYM-
BOLS 6: !Y APPLY &! PR9T DIREC;N M/ 2
DUPLICAT$4 ,^! >R[S &! ,,SYMBOLS OR
-P.DS 6: !Y APPLY M/ 2 PLAC$ ON ! SAME
BRL L9E4 ,IF AN >R[ IS 9T]IOR 6! EXPRES-
.N1 A SPACE M/ FOLL[ ! >R[4 (,SEE
,EXAMPLE #4.6-1_4)
#4.2.1-E--#4.2.2 #CI ,EXAMPLE #4.2.2-1_3 (UP-PO9T+1 #BG
VAPORIZ,N)
#2,H3,P,O4 $O ,H4,P2,O7+,H2,O$<
,EXAMPLE #4.2.2-2_3 (D[N-PO9T+1
PRECIPIT,N)
,CA3(,P,O4);2"+3,H2,S,O4
$O #2,H3,P,O4+3,CA,S,O4$%
,EXAMPLE #4.2.2-3_3 (9T]IOR D[N-PO9T+1
PRECIPIT,N)
,CA,S,O4+,NA2,CO3
$O ,CA,C,O3$% +,NA2,S,O4_4
,EXAMPLE #4.2.2-4_3 (AS -P>ISON SIGNS 9
SPATIAL >RANGE;T)
,AG,N,O3 $_33O$[33 ,AG^+" + ,N,O3"^-
,H,CL $_33O$[33 ,CL^-" + ,H^+
$_<"% $_<"%
,AG,CL$% ,H,N,O3
,EXAMPLE #4.2.2-5_3 (AS -P>ISON A#BG
SIGNS1 PR9T >RANG$ =! 3V5I;E (! PR9T]1
NORMAL DIREC;N 9 BRL)
-------------------------------------#BH
(,IN ? EXAMPLE1 ! PR9T %[S ! >R[S
WRAPP+ 9 A LOOP1 LEFT 6"R1 D[N1 & !N F
"R 6LEFT4 ,9 BRL1 ! >R[S >E >RANG$ 6BE
R1D F LEFT 6"R Z IS ! NORMAL R1D+
DIREC;N4)
#4.2.2-1--#4.2.2-5 #DA ,O A#BH
__
,C,H3,C_3],S_3],CO,A
,O ,O
,C,O2 __ __
$33333O ,H,O,C,C,H2,C_3],S_3],CO,A
,O
__
,C,H3,C_3],S_3],CO,A
$33333333333333333333O
,O ,O
__ __
,H,O,C_3],C,H_3],C_3],S_3],CO,A
_
,C_3],C,H3
__
,O
,O ,O B#BH
-,C,O2 __ __
$333333O ,C,H3,C,C,H2,C_3],S_3],CO,A
#1_4 #2@(,H@)
#2_4 -,H2,O
#3_4 #2@(,H@)
$3333333333333O
,O
__
,C,H3,C,H2,C,H2,C_3],S_3],CO,A
-------------------------------------#BI
,EXAMPLE #4.2.2-6_3 (D\# V]TICAL >R[S )
HALF-B>BS)
,A $33@O$,[33 ,B
$@<",%
,C
#4.2.2-E--#4.2.2-6 #DC ,EXAMPLE #4.2.2-7_3 (V]TICAL A#BI
>R[S PO9T+ 6A POR;N (A REAC;N)
,N,H3+,H2,O
$@<",%
,H^+"+,CL^-"+,N,H4^+"+,O,H^-
$33@O$,[33 ,N,H4^+"+,CL^-"+,H2,O
-------------------------------------#CJ
#4.2.3 ..,L1D ,L9ES & ,L1D .,>R[S4
,^! M/ 2 PRES5T$ Z DIRECT$ 9 ..,GUIDE-
L9ES = ,MA!MATICAL .,DIAGRAMS4 ,! BRLD
>R[S M/ N 2 US$4
,EXAMPLE #4.2.3-1_3 (L1D >R[S1 DIREC;N
REQUIR$)
#4.2.4 .,DIPOLE .,>R[4 ,! A#CC
DIPOLE >R[1 DENOT+ ELECTRON 4PLACE;T1 M/
2 PLAC$ Z 9 PR9T Z NE>LY Z BRL =MAT P]-
MITS4 ,IF ? >R[ IS V]TICAL OR OBLIQUE1 !
PLUS SYMBOL M/ 2 PLAC$ IMMLY ABV OR 2L !
,,SYMBOL 6: X APPLIES4 ,IF A BOND IS %[N
P>ALLEL & ADJAC5T 6! V]TICAL OR OBLIQUE
>R[1 ! F/ SYMBOL (! BOND M/ 2 ALIGN$ )!
PLUS SYMBOL (! >R[4 ,A PR9T OBLIQUE DI-
POLE >R[ IS REPRES5T$ 0! SAME SYMBOL Z !
V]TICAL DIPOLE >R[4
,EXAMPLE #4.2.4-1_3 (OBLIQUE & HORIZON-
TAL DIPOLE >R[S ) BONDS)
,O
_//
$+<
,R_3],C_3],X
$+3333O
#4.2.4--#4.2.4-1 #EC #4.2.5 .,MODIFIC,N .( .,>- B#CC
R[S4 ,>R[S MODIFI$ ABV AND_/OR 2L MAY 2
TRANSCRIB$ SPATI,Y OR1 0EMPLOY+ ! RULES
(! ,NEME? ,CODE1 HORIZONT,Y4 ,A JUDG;T
M/ 2 MADE Z 6! MO/ EASILY "U/OOD ME?OD1
DEP5D+ ON ! MAT]IAL 2+ TRANSCRIB$4 ,A
SPATIAL TRANSCRIP;N IS USU,Y ! BE/4 ,IF
A MODIFI$ >R[ IS REPRES5T$ SPATI,Y1 !
%AFT (! >R[ M/ 2 L5G!N$ 6A3OMMODATE !
L5G? (! MODIFI]4 ,! F/ CELL (! MODIFI]
M/ />T IMMLY ABV OR 2L ! F/ CELL (! >R[
%AFT4 ,! F9AL CELL (! MODIFI] M/ 2 PLAC$
IMMLY ABOVE_/BELOW ! LA/ CELL (! %AFT4
,IF ! >R[ IS MODIFI$ BO? ABV & 2L & IF !
MODIFI]S >E ( DI6]5T L5G?S1 ! %ORT]
MODIFI] M/ 2 C5T]$ ON ! %AFT4
-------------------------------------#CD
,IF ! MODIFIC,N (A S+LE >R[ IS DIVID$
S T "P (! MODIFIC,N APPE>S ABV & "P 2L !
>R[1 X IS A PR9T]'S ME?OD ( SAV+ SPACE4
,9 BRL1 ! MODIFI]S MAY 2 -PLET$ ABV !
%AFT OR PLAC$ Z 9 PR9T4 (,SEE ,EXAMPLE
#4.2.2-5) ,! DECI.N M/ 2 BAS$ ^U ! EASE
( R1D+4 ,IF ! MODIFI] IS ALL ABV ! >R[ 9
PR9T1 FOLL[ ! PR9T4 ,9 ! EV5T D\# >R[S >E MODIFI$1 A#CD
"O ABV &! O!R 2L1 ! PLACE;T (! MODIFI]S
&! L5G? (! >R[S M/ 3=M 6! PR9T NOT,N4
,IF !Y >E ( EQUAL L5G? 9 PR9T1 ! %AFTS (
BO? >R[S M/ 2 (! CORRECT L5G? 6A3OMMO-
DATE ! L;GE/ MODIFI]4 ,! %ORT] MODIFI]
M/ 2 C5T]$ ABV OR 2L ! APPROPRIATE %AFT4
(,SEE ,EXAMPLE #4.2.5-2_4)
,EXAMPLE #4.2.5-1_3 (S+LE >R[1 MODIFI$
ABV)
,C,H2_7],C,H2+,H2
,PT, ,PD, OR ,NI
$3333333333333333O ,C,H3_3],C,H3
(,IN ,EXAMPLE #4.2.5-2, ! >R[S >E ON !
DIAGONAL 9 PR9T 6PROVIDE SPAC+ 2T !
DI6]5T -PON5TS4 ,DIAGONAL & V]TICAL >R[S
& BONDS H NO *EMICAL SIGNIFIC.E 9 ?
EXAMPLE4 ,^! MAY 2 TRANSCRIB$ Z
HORIZONTAL >R[S & BONDS)
#4.2.5--#4.2.5-1 #EE ,EXAMPLE #4.2.5-2_3 (D\# >R[S1 #CE
SAME L5G?1 EA* MODIFI$)
,O#A
_//
,R_3],C,H_3],C
_ _*
^+",N,H3 ,O^-"#C
,H^+
#A$333333@O$,[333333#B
,O,H^-
,O
_//
#B,R_3],C,H_3],C
_ _*
^+",N,H3 ,O,H
,O,H^-
#C$333333@O$,[333333#D
,H^+
,O A#CE
_//
#D,R_3],C,H_3],C +,H2,O
_ _*
,N,H2 ,O^-
-------------------------------------#CF
,EXAMPLE #4.2.5-3_3 (>R[ MODIFI$ BY
C.ELL,N OR NEG,N)
G $[3O U, G /$[3O G, U /$[3O U_4 ,?US1 !
ONLY ALL[$ TRANSI;NS >E ^? 9VOLV+ A
*ANGE 9 P>;Y4
-------------------------------------#CG
#4.2.6 .,>R[ .,BONDS4 ,O3A.N,Y
>R[S >E US$ Z BONDS4 ,C>E M/ 2 TAK5 TO
4T+UI% 2T >R[ BONDS & >R[S US$ Z -P>ISON
,SIGNS4 ,IF >R[S O3UR 2T *EMICAL -P.DS1
!Y >E -P>ISON SIGNS4 ,IF !Y O3UR )9 A
-P.D OR /RUCTURE1 !Y >E BONDS4 ,3TEXT (
SURR.D! MAT]IAL W HELP ID5TIFY ! PURPOSE
(! >R[4
#D.2.5-2--#4.2.6 #EG ,EXAMPLE #4.2.6-1_3 (TWO COVAL5T A#CG
& "O COORD9ATE COVAL5T BOND)
,C"_[3]%_7]],O
,EXAMPLE #4.2.6-2_3 (COORD9ATE COVAL5T
BOND)
@,( ,H @,)^+ OR ,H
@,( ? @,) _
@,(,H?,O?,H@,) ,H_[3],O_3],H
@,( ? @,) +
,EXAMPLE #4.2.6-3_3 (>R[ BONDS )9
SPATIAL /RUCTURE)
[O [O B#CG
_// _* _/ _**
[O [O [O
#2_ __ _+,MG^2+
[O [O [O
_** _/ _* _//
[O ,N
_
,O,H
-------------------------------------#CH
[O_3][O
_// _**
_// _**
[O [O#A
_* _/
_* _/
[O_7][O
_/ _*
_/ _*
$O [O ,N#B
_** _//
_** _//
[O_3][O
#0.2.6-1--#4.2.6-3 #EI #A_3],O A#CH
_
_
_ [O_3][O
_ _// _**
_ _// _**
#B_3O],MG_[3],N [O+2,H^+
_ _* _/
_ _* _/
_ [O_7][O
_ _/ _*
_ _/ _*
,O_333][O [O
_** _//
_** _//
[O_3][O
,EXAMPLE #4.2.6-4_3 (OBLIQUE >R[ #CI
BONDS )9 SPATIAL /RUCTURE)
,H3,C ,C,H3
_* _/
,C_33],C
__ __
,O_3],N ,N_3],O
_;/ _* _/% _*
,H ,NI ,H+2,H^+
_* _/< _* _;/
,O_3],N ,N_3],O
__ __
,C_33],C
_/ _*
,H3,C ,C,H3
-------------------------------------#DJ
#4.3 .,ELECTRON .,DOT .,BONDS_4 ,AL?
ALL ELECTRON DOTS H ! SAME *EMICAL M1N+1
WRIT]S ( TEXTBOOKS USE DI6]5T TYPES (
DOT NOT,N 6ILLU/RATE A PO9T1 TRACE
TRANSF]R$ OR %>$ ELECTRONS1 DENOTE FREE
ELECTRONS1 ETC4 ,9 BRL1 ^! DI6];ES M/ 2
#4.2.6-3--#4.3 #FA MA9TA9$4 ,IF :AT APPE>S 6BE A A#DJ
BOLD DOT IS US$ &A SMALL] DOT IS N US$
ELSE": 9 ! TEXT1 ! BOLD DOT M/ 2
TRANSCRIB$ Z A REGUL> ELECTRON DOT (DOTS
#16)_4 ,O!R TYPES >E TRANSCRIB$ AC 6!
LI/ 9 ,SEC;N #3.2 ( ? ,CODE4
,:5 COLOR$ DOTS >E US$ 9 PR9T =
4T9C;N1 *OOSE "O (! DOT 3FIGUR,NS N US$
ELES": 9 ! TEXT 6REPRES5T ^! COLOR$
DOTS4 ,IF ? O3URS 9 ONLY "O PLACE1 A
TRANSCRIB]'S NOTE M/ 2 US$ 6%[ ! M1N+ (!
3FIGUR,N *OS54 ,IF ! TE*NIQUE IS US$
"?\T ! TEXT1 ? USE1 9CLUD+ ! COLOR (!
PR9T DOT1 M/ 2 NOT$ ON ! ,SPECIAL
,SYMBOLS PAGE4
#4.3.1 .,PLACE;T .( .,ELECTRON
.,DOTS4 ,ELECTRON DOTS M/ 2 PLAC$ ABV1
2L1 6! "R1 6! LEFT OR ON ! DIAGONAL Z !Y
APPE> 9 PR9T4 ,AT "TS A S+LE DOT :
APPE>S ABV1 2L1 6! "R OR LEFT (! ELE;T
MAY N 2 C5T]$ 9 PR9T1 B 9 BRL ? 4PLACE;T
IS 6BE IGNOR$ UN.S X IS ON ! DIAGONAL4
(,SEE ,EXAMPLES #4.3.1-3, #4.3.1-4 &
#4.3.1-5_4)
,:5 DOTS APPE> ON ! DIAGONAL 6! ELE;T 9 PR9T1 ! SYMBOL M/ 2 LOCAT$ 6! B#DJ
"R OR LEFT (! ,,SYMBOL 9 BRL ON ! L9E
IMMLY ABOVE_/BELOW 9 ! F/ CELL PREC$+ OR
FOLL[+ ! ,,SYMBOL 6: X APPLIES4 ,:5 A
.PAIR ( ELECTRON DOTS APPE>S ON !
DIAGONAL 6! ELE;T1 ! LEFT-MO/ DOT (!1
PAIR IS 3SID]$ ! 8LEFT0 DOT 9 SELECT+ !
CORRECT SYMBOL 6USE (FROM ! LI/ 9 ,SEC;N
#3.2.1)_4 ,IF "! >E TWO SETS ( DOTS ON !
DIAGONAL 9 PR9T1 !Y %D 2 PLAC$ "O
DIRECTLY "U ! O!R1 ON ! DIAGONAL 6!
,,SYMBOL4 ,H["E1 !Y MAY 2 PLAC$
DIAGON,Y 6EA* O!R :5 X IS NEC TO AVOID
3FU.N ) O!= NOT,N 9 ! /RUCTURE4 (,SEE
,EXAMPLE #4.3.1-11_4)
,EXAMPLE #4.3.1-1_3 (ALL DOTS1 S+LE OR
D\#1 ID5TICAL 9 SIZE & %APE)
*
?,F?
?
#4.2.6--#4.3.1 #FC ,EXAMPLE #4.3.1-2_3 (DI6]5T TYPES #DA
( DOTS)
,H ,H
& $
,H&,C:,C%,H
] %
,H ,H
,EXAMPLE #4.3.1-3_3 (S+LE DOTS1 C5T]$ 9
PR9T)
?
*,O?
*
,EXAMPLE #4.3.1-4_3 (S+LE DOTS N C5T]$
ON ! ,,SYMBOL 9 PR9T)
?
*,O?
*
,EXAMPLE #4.3.1-5_3 (S+LE DOT A#DA
APPE>S 6BE 9 SUBSCRIPT POSI;N 9 PR9T)
?
?,O*
?
,H
,EXAMPLE #4.3.1-6_3 (TRIPLETS)
,',! F/ TRIPLET IS V]TICAL &!
SECOND IS HORIZONTAL 9 PR9T4,'
?,N\,N? OR ,H?,C\,C?,H
-------------------------------------#DB
,EXAMPLE #4.3.1-7_3 (/RUCTURE 5CLOS$ 9
GR\P+ SIGNS ) SUP]SCRIPT)
@,( # @,)^3-
@,( #,O# @,)
@,( # ? # @,)
@,(:,O],P&,O>@,)
@,( # & # @,)
@,( #,O# @,)
@,( : @,)
#4.3.1-2--#4.3.1-7 #FE ,EXAMPLE #4.3.1-8_3 (DOTS 9 R+ A#DB
/RUCTURE)
,H
,H _ ,H
_* _ _/
,H ?,O? ,C
_* __ _
,H_3],C ,C ,N
_/ _* _/ _* _/ ? _*
,H ,N? ,C ,C_3],H
_ __ __
,C ,C_3333],N
_// _* ? _/ ?
?,O ,N
? _
,C
_/ _ _*
,H _ ,H
,H
,EXAMPLE #4.3.1-9_3 (DOTS -B9$ ) #DC
O!R NOT,N @(DELTA--"PTIAL *>GE@))
?
.D^+",H?,O?.D^-
?
,H
.D^+
,EXAMPLE #4.3.1-10_3 (DOTS -B9$ )
SUP]SCRIPT)
? ?
,MG[+2*,BR? $O ,MG^2+1+2%,BR?^-
* $
#4.3.1-8--#4.3.1-10 #FG ,EXAMPLE #4.3.1-11_3 (DIAGONAL A#DC
DOTS)
?
? ? ,O?
,O ?
# ? #
#,S #,S
# # ?
? ,O
,O? ? ?
?
,EXAMPLE #4.3.1-12_3 (DOTS & LRS 9
COLOR$ PR9T)
,',IN ? /RUCTURE1 ;,H_'S, ;,N &!
DOTS %[N Z [ >E 9 BLUE PR9T4,'
,F ,H
? [
,F?,B[,N[,H
? [
,F ,H
,EXAMPLE #4.3.2-1_3 (DOTS M1N A#DD
RATIO1 N ELECTRON DOTS)
,RELATIVE NUMB] ( ATOMS3
,C "1 ,H .K #6.25 "1 #24.8
,SMALLE/ RATIO ( ATOMS3
?6.25/6.25# "1 ?24.8/6.25#
.K #1 "1 #4
,EMPIRICAL FORMULA .K ,C,H4
-------------------------------------#DE
,EXAMPLE #4.3.2-2_3 (DOTS M1N RATIO1 N
ELECTRON DOTS)
,HG "1 ,NA "1 ,AL
#0.0300 "1 #0.0600 "1 #0.0200
#3 "1 #6 "1 #2
#4.4 .,O!] .,BONDS4 ,ALL (! FOLL[+
BONDS MAY 2 EXT5D$ 6A3OMMODATE SURR.D+
,MAT]IAL4 (,SEE ,EXAMPLES #4.4.3-1,
#4.4.3-6, & #4.4.3-19_4)
#4.4.1 .,HORIZONTAL .,BONDS4
,HORIZONTAL BONDS >E EMPLOY$ 9 BO?
SPATIAL & NON-SPATIAL /RUCTURES4 ,!Y >E
#4.3.2-1--#4.4.-2 #GA SUBJECT 6,NEME? ,CODE ,RULE ,,XIX A#DE
(,OP],N ,SIGNS)_4 ,SEE ,SEC;N #1.1 ( ?
,CODE = 3/RUC;N ( HORIZONTAL BONDS4 ,IF
NUMB]S OR O!R NOT,N APPE> ABV AND_/OR 2L
"S (! ,,SYMBOLS OR SYMBOLS1 ! >RANGE;T
IS SPATIAL4 ,SEE ,SEC;N #5.3 = PLACE;T (
NUMB]S & O!R NOT,N4
,EXAMPLE #4.4.1-1_3 (HORIZONTAL BONDS2
NO -P>ISON SIGN2 RUNOV]S REQUIR$2
4PLAY$ B N SPATIAL)
,C,H3_3],C,H2_3],C,H2_3],C,H2_3],C,H2
_3],O_3],C,H2_3],C,H2_3],C,H2
_3],C,H2_3],C,H2_3],C,H3
,EXAMPLE #4.4.1-2_3 (HORIZONTAL BOND2
4PLAY$2 SPATIAL 2C ( ELECTRON DOTS
OVER_/UNDER ,,SYMBOL)
?
,BR_3],BR $33O$[33 #2?,BR*
?
,EXAMPLE #4.4.1-3_3 (HORIZONTAL #DF
BONDS2 4PLAY$2 SPATIAL 2C C>BON ATOMS
>E NUMB]$)
#1 #2 #3 #4
,C,H2_7],C,H_3],C,H2_3],C,H3
#4.4.2 .,V]TICAL .,BONDS4
,/RUCTURES 3TA9+ V]TICAL OR OBLIQUE
BONDS >E ALW 3SID]$ 6BE SPATIAL >RANGE-
;TS &1 9 BRL1 REQUIRE A BLANK L9E PREC$+
& FOLL[+ ! /RUCTURE1 :E!R EMB$D$ OR
4PLAY$4 ,Z ) HORIZONTAL BONDS1 ! PR9T
TYPE ( BOND1 M/ 2 DUPLICAT$ 9 BRL4
#4.4.3 .,=MAT4 ,A S+LE V]TICAL
BOND M/ 2 ALIGN$ )! F/ LR (! ,,SYMBOL 6:
X APPLIES4 ,:5 BONDS 3SI/+ ( TWO OR M
CELLS APPLY 6A S+LE-LR ,,SYMBOL1 ! F/
CELL (! BOND %D 2 ALIGN$ )! CAPITALIZ,N
9DICATOR4 ,IF ! ,,SYMBOL 3SI/S ( #2 OR M
LRS1 ! F/ CELL (A #2-CELL BOND M/ 2
ALIGN$ )! F/ LR (! ,,SYMBOL4
,OBLIQUE BONDS >E BRLD 6! "R OR LEFT (
! ,,SYMBOL 6: !Y APPLY1 ON A SEP>ATE L9E
#4.4.1--#4.4.3 #GC BELOW_/ABOVE ! ,,SYMBOL Z 9DICAT$ A#DF
0! PR9T4 ,OBLIQUE BONDS C 2 TRANSCRIB$ Z
OBLIQUE1 V]TICAL OR HORIZONTAL IF ! PR9T
USES OBLIQUE BONDS SIMPLY 6A3OMMODATE !
O!R NOT,N PRES5T4 .,EXCEP;N3 ,9 R+
/RUCTURES ! OBLIQUE BONDS M/ 2 TRAN-
SCRIB$ Z 9 PR9T 6PRES]VE ! %APE (!
/RUCTURE4
,9 CYCLICAL OR R+ /RUCTURES1 "S LEEWAY
IS ALL[$ 9 ORD] 6DUPLICATE ! PR9T %APE4
,H["E1 ! BONDS M/ 2 >RANG$ 9 S* A WAY T
! R1D] HAS NO D\BT Z 6: ,,SYMBOL ! BOND
APPLIES4
,:5 V]TICAL BONDS APPE> ABV OR 2L
UNLABEL$ V]TICES1 ! BOND %D NORM,Y 2
ALIGN$ )! 8\T]0 CELL (! TWO-CELL SYMBOL4
,H["E1 X MAY 2 ALIGN$ )! 89N]0 CELL (!
TWO-CELL SYMBOL 9 ORD] 6AVOID 3FU.N )
O!R NOT,N4 (,SEE ,EXAMPLE #4.2.1-5_4)
,4PLAY$ EXPRES.NS %D 2 9D5T$ TWO CELLS
6! "R (! M>G9 B MAY />T AT ! M>G9 IF 0S
DO+ ! /RUCTURE OR AN 9TEGRAL POR;N (!
/RUCTURE C 2 KEPT 9TACT4 ,X IS CRUCIAL
6AVOID RUNOV]S )9 A R+4
,EXAMPLE #4.4.3-1_3 (HORIZONTAL #DG
BONDS EXT5D$ 6A3OMMODATE O!R NOT,N)
,H
_
,H ,H_3],C_3],H ,H ,H
_ _ _ _
_3],C_3333],C_7777],C_3],C_3]
_ _
,H ,H
,EXAMPLE #4.4.3-2_3 (9COMPLETE SPATIAL
>RANGE;T 4PLAY$ 6N>RATIVE TEXT2
PUNCTU,N FOLL[+ BOND)
,9 ,SEC;N #29.17 WE F.D T C>BOXYLIC
ACIDS REACT$ ) AM9ES 6=M AMIDES4
,O ,H
__ _
_3],C_3],N_3]_4
,AM9O ACIDS >E L9K$ "? ! SAME 3D5S,N
PROCESS4 ,H["E1 BIO*EMI/S CALL ! AMIDE
#4.4.3--#4.4.3-2 #GE L9K A .PEPTIDE .BOND4 ,! NEW A#DG
MOLECULE
-------------------------------------#DH
,EXAMPLE #4.4.3-3_3 (HORIZONTAL1
V]TICAL1 & OBLIQUE BONDS)
,H
_
,H_3],C_3],H
_
,H_3],C_=],C_3],C ,H ,H
_** _ _
,C_3],C_3],O
_ _
,H ,H
,EXAMPLE #4.4.3-4_3 (HORIZONTAL1 V]TI-
CAL & OBLIQUE BONDS2 V]TICAL BONDS
EXT5D$ 6A3OMMODATE ! OBLIQUE BONDS2
.;,R REPRES5TS A *EMICAL GR\P @(,SEC4
#9.4_4@))
,O A#DH
_//
.;,R_3],C_3],O_3],C,H2
_
,O _
_// _
.;,R'_3],C_3],O_3],C,H
_
,O _
_// _
.;,R''_3],C_3],O_3],C,H2
-------------------------------------#DI
,EXAMPLE #4.4.3-5_3 (/RUCTURE ) DOTT$
HYDROG5 BOND)
,H
_
_3],C_3],C
_
,N ,H
_/ _* _/
,H ,H_1],O
_*
,H
#4.4.3-3--#4.4.3-5 #GG ,EXAMPLE #4.4.3-6_3 (/RUCTURE ) #EJ
_;G BROK5 BOND 9DICAT+ A W1K BOND2
RUNOV]S)
,GUAN9E
,H
_
,N_3],H#A
_/
,R ,N_7][O
_* _/ _*
,N_3][O ,N_3],H#B
_/ _** _/
[O [O_3][O
_** _/ _**
_** _/ ,O#C
,N
,CYTOS9E A#EJ
#A_22222222],O ,R
_** _/
[O_3],N
_/ _*
#B_22222222],N [O
_** _//
[O_3][O
_/
#C_22],H_3],N
_
,H
-------------------------------------#EA
,EXAMPLE #4.4.3-7_3 (DOTT$ BONDS)
,ACTIVAT$ -PLEX
,C,H3
_
,O_1],C_1],I
_/ _2 _V
,H ,H _V
,H
#4.4.3-6--#4.4.3-7 #GI ,EXAMPLE #4.4.3-8_3 (V>IETY ( A#EA
BONDS)
,C,H3
_*
,H,O^-"+ ,C_3],I
_2/ _V
,H ,H
,C,H3
_
$O ,O_1],C_1],I
_/ _2/ _V
,H ,H ,H
,H_3],O
_*
$O ,C_3],C,H3+,I^-
_2/ _V
,H ,H
,EXAMPLE #4.4.3-9_3 (DOTS #EB
REPRES5T+ OMIS.NS1 N BONDS)
,H ,H
_ _
,H_3],N_3](,C,H2);6"_3],N_3],H
,O ,O
__ __
+,H_3],O_3],C_3](,C,H2);4"_3],C
_3],O_3],H
,H ,O
_ __
$O ''' _3],N_3],C_3] ''' +,H2,O
#4.4.3-8--#4.4.3--9 #HA ,EXAMPLE #4.4.3-10_3 (/RUCTURE A#EB
3TA9+ V]TICAL WAVY BOND)
,BR
_9
[O
_/ _*
[O [O
_ _
[O [O
_* _/
[O
_
,C(,C,H3);3