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Crystal Structures of 8‐Methoxy‐ and 8‐Nitronaphthonitrile; Intramolecular Nucleophile‐electrophile Interactions
Author(s) -
Procter Garry,
Britton Doyle,
Dunitz Jack D.
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640211
Subject(s) - chemistry , electrophile , intramolecular force , planarity testing , nucleophile , molecule , bent molecular geometry , nitro , crystallography , atom (system on chip) , distortion (music) , crystal structure , crystal (programming language) , stereochemistry , organic chemistry , catalysis , amplifier , programming language , alkyl , cmos , electronic engineering , computer science , engineering , embedded system
The crystal structures of 8‐methoxy‐1‐naphthonitrile and 8‐nitro‐1‐naphthonitrile have been determined by X‐ray analysis. The methoxynitrile molecule shows a distortion pattern that is essentially similar to that found previously in other 1,8‐disubstituted naphthalenes with Nu…CO interactions; instead of non‐planarity at the carbonyl C‐atom there is bending at the the cyano C‐atom. Crystals of the nitronitrile contain two symmetry‐independent molecules that differ in structure; both show bent cyano groups, short O…CN distances, and asymmetric nitro groups, but in different degree. There is no clear correlation between the amount of any given distortion and the strength of the nucleophile‐electrophile interaction.