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Analysis of inter‐ring coupling effects in N ‐heterobicyclic π‐systems using a structural definition of aromaticity
Author(s) -
Gready Jill E.
Publication year - 1987
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560310308
Subject(s) - aromaticity , electron delocalization , ring (chemistry) , tautomer , chemistry , delocalized electron , computational chemistry , bicyclic molecule , coupling (piping) , bond order , substitution (logic) , bond length , pteridine , natural bond orbital , stereochemistry , crystallography , density functional theory , molecule , crystal structure , materials science , computer science , organic chemistry , enzyme , programming language , metallurgy
A purely structural definition of aromaticity based on the average ring bond length and ‐bond order is proposed. The definition is illustrated for N ‐heterocycles by reference to theoretical STO‐3G and 3‐21G geometries and charges for some pteridine derivatives. The treatment focuses on the gross structural changes (i.e., ring size, overall degree of π‐electron delocalization, and net ring charges), accompanying chemical changes, such as substitution, tautomerization, ring reduction, and deazination, as well as the structural interdependence of the two rings in a bicyclic ring system.