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Theoretical study of the internal rotational barriers in nitrobenzene, 2‐nitrotoluene, 2‐nitrophenol, and 2‐nitroaniline
Author(s) -
Chen P. C.,
Chen S. C.
Publication year - 2001
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.1069
Subject(s) - nitrobenzene , nitro , chemistry , nitrophenol , molecule , nitroaniline , planar , density functional theory , internal rotation , computational chemistry , group (periodic table) , nitro compound , crystallography , organic chemistry , catalysis , mechanical engineering , alkyl , computer graphics (images) , computer science , engineering
The molecular geometries and internal rotational barriers of the nitro group of nitrobenzene (NB), 2‐nitrotoluene (2‐NT), 2‐nitroaniline (2‐NA), and 2‐nitrophenol (2‐NP) were calculated by five different types of density functional theory (DFT) methods with three different levels of basis sets. Analysis of the torsional angles of the nitro, methyl, amino, and hydroxyl groups indicate that NB, 2‐NA, and 2‐NP are planar molecules, but 2‐NT is not a planar molecule. Internal rotational barriers of the nitro group were calculated as V 2 barriers, and the NO 2 torsional potentials for each molecule were given. The values of the V 2 barriers depend on the DFT methods and basis sets. The average values of the V 2 barriers for NB, 2‐NT, 2‐NA, and 2‐NP are 6.47 kcal/mol, 3.00 kcal/mol, 10.20 kcal/mol, and 13.26 kcal/mol, respectively. © 2001 John Wiley & Sons, Inc. Int J Quant Chem 83: 332–337, 2001