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Crystal and moecular structure of N ‐nitro‐ N ‐methyl‐ p ‐nitroaniline: Analysis of substituent effects on the ring geometry and estimation of the Hammett substituent constant for the N ‐methylnitramino group
Author(s) -
Anulewicz Romana,
Krygowski Tadeusz Marek,
Gawinecki Ryszard,
Rasała Danuta
Publication year - 1993
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610060502
Subject(s) - chemistry , substituent , nitro , nitrobenzene , molecular geometry , ring (chemistry) , quantitative structure–activity relationship , crystal structure , bond length , geometry , computational chemistry , hammett equation , crystallography , stereochemistry , molecule , organic chemistry , reaction rate constant , mathematics , quantum mechanics , alkyl , catalysis , physics , kinetics
Abstract The crystal and molecular structure of N ‐nitro‐ N ‐methyl‐ p ‐nitroaniline was solved with good precision: R = 0·058 and average estimated standard deviation for bond lengths = 0·003 Å. Analysis of the geometry reveals that the NO 2 attached to the N atom is strongly conjugated. Application of the HOSE model to its geometry and to geometries of 12 other para ‐substituted nitrobenzenes yields good linear regressions between canonical structure weights and Hammett σ values by interpolation, σ for the N(Me)NO 2 group is estimated to 0·36.