EDITING ORGANIC ABSTRACTS FOR CHEMICAL ABSTRACTS* By ROBERT E. STOBAUGH Senior Associate Editor, Chemical Abstracts Service, The Ohio State University, Columbus, Ohio
A b s t r a c t s of both j o u r n a l a r t i c l e s and pate n t s a r e published by C h e m i c a l A b s t r a c t s a n d , i n g e n e r a l , r e q u i r e t h e s a m e kind of e d i t o r i a l attention and p r e s e n t similar p r o b l e m s . Abs t r a c t s m u s t be of a n i n f o r m a t i v e n a t u r e , but they m u s t a l s o be noncritical. The a b s t r a c t o r is a s k e d t o p r e s e n t the a u t h o r ' s conclusions without e x p r e s s i n g h i s own opinion of the w o r k . T h i s f a c t is kept i n mind by the e d i t o r , who a t t h e s a m e t i m e m u s t not e d i t f r o m a biased viewpoint. C r i t i c a l editing is allowed only t o t h e extent of r e j e c t i n g a r t i c l e s obviously v a l u e l e s s as c h e m i c a l contributions. Judgment as t o t h e r e l a t i v e i m p o r t a n c e of a r t i c l e s is l e f t t o the u s e r s of the j o u r n a l . A b s t r a c t s f o r all of t h e s e c t i o n s of C h e m i c a l A b s t r a c t s a r e edited f o r c h e m i c a l a c c u r a c y , length, p r o p e r technical language, c l e a r n e s s of e x p r e s s i o n , and the u s e of s t a n d a r d f o r m s , C o r r e l a t i o n of a b s t r a c t s , involving C h e m i c a l A b s t r a c t s r e f e r e n c e s , and c l a s s i f i c a t i o n as t o s e c t i o n of the j o u r n a l , including the u s e of c r o s s r e f e r e n c e s , also receive editorial attention. E v e r y a t t e m p t i s m a d e t o a s s i g n e a c h abs t r a c t o r w o r k i n h i s own f i e l d s of s p e c i a l i n t e r e s t and e x p e r i e n c e . However, t h e r e a r e v a r i a t i o n s in e x p e r i e n c e i n a b s t r a c t i n g and in s k i l l of conc i s e e x p r e s s i o n . It is all too e a s y t o m i s c o p y o r m i s t r a n s l a t e a few w o r d s or t o o m i t a s t e p i n a p r o c e s s and by doing s o , l e s s e n the value of a n abstract. A b s t r a c t o r s s o m e t i m e s have difficulty r e c onciling brevity with t h e u s e of good i d i o m a t i c E n g l i s h and m a y u s e a t e l e g r a p h i c s t y l e . An e x p r e s s i o n s u c h as "the s o l i d w a s heated with a n a c i d chloride i n the p r e s e n c e of a t e r t i a r y base" r e a d s m u c h b e t t e r t h a n "solid h e a t e d with a c i d chloride i n p r e s e n c e of t e r t i a r y base." T h i s s t y l e of writing is no m o r e d e s i r a b l e t h a n t h e following v e r b o s e example: "In a similar m a n n e r , v a l e r i c a c i d ethyl e s t e r w a s saponified during a period of two h o u r s a t a t e m p e r a t u r e of 50' t o l e a d t o the production of v a l e r i c a c i d i n a yield of 80% of theoretical." T h i s s e n t e n c e i s i m p r o v e d by condensation t o " S i m i l a r l y , E t v a l e r a t e w a s sapond. during 2 h r . a t 50° t o give v a l e r i c acid in 80% yield." Two s p a c e - s a v i n g d e v i c e s which a r e u s e d extensively a r e R o m a n n u m e r a l s and f o r m u l a s . A R o m a n n u m e r a l , i n boldface t y p e , m a y be e n t e r e d parenthetically following the f i r s t a p p e a r a n c e i n the body of a n a b s t r a c t of a r e c u r r i n g name and then substituted f o r t h a t n a m e throughout the r e m a i n d e r of the a b s t r a c t . R o m a n num e r a l s a r e used strictly to replace repeated w o r d s and not to indicate c h e m i c a l r e l a t i o n s h i p s between s u b s t a n c e s . They should not be u s e d a s
s u b s t i t u t e s f o r s u b s t a n c e s f o r which t h e n a m e s or f o r m u l a s a r e r e l a t i v e l y s h o r t , as u r e a and CSz. It is p a r t i c u l a r l y i m p o r t a n t t h a t t h e num e r a l s be introduced i n consecutive o r d e r without skipping. T h i s p r a c t i c e is n e c e s s a r y , bec a u s e , i n o r d e r t o d e t e r m i n e t h e meaning of a given n u m e r a l , it is n e c e s s a r y t o r e f e r t o the point of i t s introduction. In a n a b s t r a c t which includes a l a r g e n u m b e r of R o m a n n u m e r a l s , a s many do, i t is v e r y difficult t o identify a given n u m e r a l u n l e s s i t h a s been introduced i n consecutive o r d e r . F o r m u l a s a r e often g r e a t s p a c e and t i m e s a v e r s . In 'the O r g a n i c Section, m o l e c u l a r , s e m i s t r u c t u r a l , and s t r u c t u r a l f o r m u l a s a r e u s e d . Molecular f o r m u l a s l i s t the e l e m e n t a l composition of a s u b s t a n c e , A s e m i s t r u c t u r a l f o r m u l a is a breakdown of a m o l e c u l a r f o r m u l a , s i n c e the basic n u c l e u s , substituting g r o u p s , and n u m e r i c a l positions of s u c h g r o u p s a r e given. F o r e x a m p l e , 2,4-dibromobenzoic a c i d can be r e p r e s e n t e d by the m o l e c u l a r f o r m u l a C 7 H 4 0 2 B r 2 , and by the s e m i s t r u c t u r a l f o r m u l a 2,4-Br2CgH3C02H. F r o m the s e m i s t r u c t u r a l f o r m u l a , the r e a d e r c a n supply the a r r a n g e m e n t of a t o m s i n t h e compound, In a s t r u c t u r a l f o r m u l a t h e a c t u a l a r r a n g e m e n t is d r a w n , and t h e points of a t t a c h m e n t of the substituents a r e indic a t e d . In m a n y c a s e s t h e s p a c e r e l a t i o n s h i p between the substituents is shown. A s e m i s t r u c t u r a l f o r m u l a is p r e f e r r e d if i t is cons i d e r a b l y s h o r t e r than the n a m e of the compound and if t h e t r a n s f o r m a t i o n of the n a m e into the f o r m u l a i s not t i m e - c o n s u m i n g . C h e m i c a l n a m e s a r e not changed, as a r u l e , t o n a m e s u s e d i n the i n d e x e s and conforming t o IUPAC r e g u l a t i o n s . The n o m e n c l a t u r e of the author is maintained i n a b s t r a c t s of h i s w o r k f o r s e v e r a l r e a s o n s : ( 1 ) T h i s policy k e e p s t h e Organic Section in s t e p with t h e j o u r n a l as a whole. Organic c h e m i s t r y is not p e c u l i a r t o the Organic Section, and t h e o t h e r s e c t i o n s r e t a i n the o r i g i n a l n o m e n c l a t u r e i n m o s t c a s e s . ( 2 ) By maintaining a r e c o r d of new and unusual nom e n c l a t u r e i n t h e t e x t of C h e m i c a l A b s t r a c t s , the p r o c e s s of identifying a s t r u c t u r e with a given n a m e often is quickened. Such i n f o r m a t i o n often is r e q u i r e d i n working with t h e o r i g i n a l publication, and i t is d e s i r a b l e t o have i t l o c a t e d i n a single r e f e r e n c e w o r k , C h e m i c a l A b s t r a c t s . ( 3 ) It m a k e s e a s i e r the organization of t i t l e s under a given a u t h o r ' s n a m e i n the author index. ( 4 ) It avoids e r r o r s , s i n c e e v e r y change m a d e f r o m the o r i g i n a l i n c r e a s e s t h e possibility of a m i s t a k e . ( 5 ) It s a v e s a c o n s i d e r a b l e amount of editorial time. The Organic Section is divided into t e n s e c t i o n s . The s e c t i o n s a r e , i n o r d e r of t h e i r
*Presented before t h e Division of Chemical Literature, ACS National Meeting, Chicago, Ill., September, 1958.
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EDITING ORGANIC ABSTRACTS
a p p e a r a n c e : g e n e r a1 o r g a n i c c h e m i s t r y , aliphatic compounds , a combination of c a r b o h y d r a t e s , a m i n o a.cids, f a t s , and p r o t e i n s , a l i c y c l i c compounds, benzene d e r i v a t i v e s , polynuclear condensed c a r b o c y c l i c compounds, h e t e r o c y c l i c compounds, a l k a l o i d s , t e r p e n e s , and s t e r o i d s . T h e s e s t a r t with compounds of r e l a t i v e l y s i m p l e s t r u c t u r e s and p r o c e e d t o m o r e c o m p l i c a t e d o n e s . Within e a c h s e c t i o n , j o u r n a l a b s t r a c t s a r e placed f i r s t , followed by patent a b s t r a c t s . The a b s t r a c t is c l a s s i f i e d by s e c t i o n a f t e r editing. An a b s , t r a c t which t r e a t s of compounds of a v a r i e t y of s t r u c t u r e s is placed in the s e c t i o n containing the rnost c o m p l i c a t e d s t r u c t u r e . While the atbstract is c e r t a i n l y not d e s i g n e d o r intended to tie a s u b s t i t u t e f o r t h e o r i g i n a l a r t i c l e , i t is s u p p o s e d t o r e p o r t or m a k e s p e c i f i c r e f e r e n c e to all. the new m a t e r i a l of c h e m i c a l i n t e r e s t t h a t the a r t i c l e c o n t a i n s . T h i s i n c l u d e s new m e a s u r e m e n t s , o b s e r v a t i o n s , m e t h o d s , a p p a r a t u s , t h e o r y , and compounds , as well a s previously-known s u b s t a n c e s f o r which new d a t a a r e given. In r e l a t i o n t o t h i s a s p e c t of c o m p l e t e n e s s , e v e r y e f f o r t is m a d e t o include in the a b s t r a c t r e f e r e n c e s t o p r e v i o u s l y published a b s t r a c t s of p a p e r s on the s a m e or r e l a t e d s u b j e c t s . T h e s e r e f e r e n c e s include t h a t t o t h e p r e c e d i n g c o n t r i bution f o r a b s t r a c t s of a n u m b e r e d s e r i e s a p p e a r i n g u n d e r a. g e n e r a l s u b j e c t , as well a s r e f e r e n c e s to e a r l i e r w o r k of t h e a u t h o r o r o t h e r s . If a C h e m i c a l A b s t r a c t s r e f e r e n c e t o e a r l i e r r e l a t e d w o r k i s not a v a i l a b l e , the o r i g i nal j o u r n a l or patent r e f e r e n c e is supplied. E d i t o r i a l e x p e r i e n c e , in t i m e , p r o v i d e s a s o r t of s i x t h s e n s e which t e l l s the e d i t o r when he should consult the o r i g i n a l t o s a f e g u a r d a b s t r a c t s f r o m o m i s s i o n s o r m i s t a k e s . As a n e x a m p l e , the ed.itor m a y s u s p e c t t h a t s o m e compounds p r e p a r e d have been o m i t t e d f r o m a n a b s t r a c t , or tha.t a m e l t i n g point h a s been m i s copied. The e d i t o r d o e s not r o u t i n e l y consult the o r i g i n a l a r t i c l e f o r e a c h a b s t r a c t . He c a n not, s i n c e he l a c k s t i m e t o do s o . M o r e o v e r , the j o u r n a l itself m a y not be a v a i l a b l e t o h i m . If t h e editing p r o c e s s u n c o v e r s a need for consulting the a r t i c l e a n d i t is not a v a i l a b l e , the o r i g i n a l m a y s o m e t i m e s be obtained o n a n i n t e r l i b r a r y l o a n . In s o m e c a s e s , t h e a b s t r a c t is r e t u r n e d t o t:he a b s t r a c t o r f o r c l a r i f i c a t i o n . In e i t h e r c a s e , ,a d e l a y i n publication r e s u l t s . E r r o r s i n t.he a b s t r a c t o r i g i n a t i n g f r o m e r r o r s in the o r i g i n a l a r t i c l e a l s o c a u s e e d i t o r i a l p r o b l e m s . What w a s intended i n t h e a r t i c l e m a f be obvious , and t h e m i s t a k e c a n be c o r r e c t e d by t h e a b s t r a c t o r o r e d i t o r . If s u c h is not the c a s e , the e x p r e s s i o n involved is p r i n t e d as i t is given, e i t h e r i n quotation m a r k s , or followed by the p a r e n t h e t i c w o r d " s i c " a s a n
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indication t h a t the e x p r e s s i o n is t a k e n v e r b a t i m f r o m the o r i g i n a l . Both the e d i t o r and a b s t r a c t o r m a y be b e s e t with language difficulties, the e d i t o r with the language of the o r i g i n a l a r t i c l e , and the a b s t r a c t o r with E n g l i s h . E i t h e r o n e , o r a c o m b i nation of t h e m , c a n c o m p l i c a t e the editing p r o c e s s a great deal. P a t e n t s p r e s e n t not only the p r o b l e m s a l r e a d y given, but a l s o additional o n e s , b e c a u s e of d i f f e r e n c e s i n s t y l e and point of view o r p r e s e n t a t i o n . Among the pitfalls p r e s e n t is t h e question of what t o include in the a b s t r a c t , s i n c e t h e r e m a y not be a c l e a r - c u t d i s t i n c t i o n as to w o r k which h a s been done and t h a t which m a y o r c a n be done. The language s o m e t i m e s o b s c u r e s important chemical information. For e a c h subdivision of the O r g a n i c Section t h e r e is a t l e a s t one " s e c t i o n e d i t o r , " a s p e c i a l i s t in the p a r t i c u l a r field f r o m outside the C h e m i c a l A b s t r a c t s office. The s e c t i o n e d i t o r s play a n i m p o r t a n t p a r t in controlling the quality of the s e c t i o n . F r o m t h e i r e x a m i n a t i o n of p r o o f , they check t h e a b s t r a c t s f o r c h e m i c a l s o u n d n e s s . T h e i r advice h e l p s t o g e n e r a t e and a d m i n i s t e r p o l i c i e s of the s e c t i o n . The m a t e r i a l s e n t to the p r i n t e r d i f f e r s f r o m m o s t of the p r i n t e r ' s r a w m a n u s c r i p t in t h a t the e d i t o r h a s changed the a b s t r a c t o r ' s f i n a l copy p e r h a p s c o n s i d e r a b l y . The p r i n t e r m a y have v e r y rough a n d , f r o m t h e viewpoint of f o r m , v e r y unfinished m a t e r i a l with which t o w o r k . The a b s t r a c t s the p r i n t e r r e c e i v e s have not been r e t y p e d , with v e r y few e x c e p t i o n s . The p r i n t e r s e n d s galley proof f o r the e n t i r e s e c t i o n t o the C h e m i c a l A b s t r a c t s office and proof f o r e a c h subdivision t o the s e c t i o n e d i t o r . The office proof is r e a d by t h e e d i t o r s f o r c h e m i c a l s e n s e , e r r o r s in f o r m , g r a m m a r , s p e l l i n g , and the l i k e . S p e c i a l w o r k e r s c h e c k the proof a g a i n s t copy f o r the s p e l l i n g s of a u t h o r n a m e s , r e f e r e n c e s , n u m e r i c a l d a t a , and l i k e i t e m s which cannot be judged by the e d i t o r o n the b a s i s of h i s c h e m i c a l and 0the.r knowledge. The e d i t o r e v a l u a t e s and i n c o r p o r a t e s c o r r e c t i o n s by t h e s e s p e c i a l w o r k e r s and by t h e s e c t i o n e d i t o r i n h i s own p r o o f r e a d i n g before r e t u r n i n g the g a l l e y proof t o the p r i n t e r . With t h i s s t e p , the e d i t o r ' s job is c o m p l e t e , f o r one number. In s u m m a t i o n , it is the duty of the e d i t o r t o catch slips in translation, in technical lang u a g e , i n c l e a r e x p r e s s i o n , and in adequate coverage. Particularly f o r Organic chemistry, h e m u s t s e e t o it t h a t a l a r g e amount of d e t a i l e d i n f o r m a t i o n is c o m p r e s s e d into a s m a l l s p a c e . T h e a b s t r a c t is the d e v i c e u s e d f o r c o v e r i n g t h e w o r l d ' s c h e m i c a l l i t e r a t u r e . It is t h e r e sponsibility of the e d i t o r t h a t i t be c o m p l e t e , a c c u r a t e , and c o n c i s e .
