Intramolecular hydrogen bonding and molecular structure of 2-nitroresorcinol from gas-phase electron diffractionстатья
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Дата последнего поиска статьи во внешних источниках: 14 февраля 2019 г.
Авторы:
Borisenko K.B. ,
Hargittai I.
Журнал:
The Journal of physical chemistry
Том:
97
Номер:
16
Год издания:
1993
Издательство:
American Chemical Society
Местоположение издательства:
United States
Первая страница:
4080
Последняя страница:
4084
DOI:
10.1021/j100118a025
Аннотация:
The molecular structure of 2-nitroresorcinol has been determined by electron diffraction in the gas phase. The formation of strong intramolecular hydrogen bonding between the nitro group oxygen and hydroxy hydrogen is indicated by the short H⋯O nonbonded distance, 1.76 ± 0.04 Å. The O⋯O nonbonded distance (between the nitro and hydroxy groups), 2.56 ± 0.01 Å, is also much shorter than twice the oxygen van der Waals radius. The hydrogen bond makes a 110.5 ± 1.5° angle with the N=O bond corresponding to the direction where one of the oxygen lone pairs of electrons is anticipated. There are considerable bond length changes, as compared with nitrobenzene and phenol, consistent with strong resonance-assisted hydrogen bonding. In addition to the through-bond interactions connected with the H⋯O bond formation, angular changes suggest a through-space repulsive intersubstituent effect. The benzene ring geometry indicates a marked departure from additivity of individual substituent effects. The molecular geometry of 2-nitroresorcinol is characterized by the following bond lengths (rg) and bond angles: N=O, 1.239 ± 0.003 Å; N-C, 1.449 ± 0.007 Å; (C-C)mean, 1.404 ± 0.003 Å; C1(N)-C2, 1.426 ± 0.005 Å; C2-C3/C3-C4, 1.393 ± 0.004 Å; (C-H)mean, 1.090 ± 0.015 Å; C-O 1.354 ± 0.004 Å; O-H, 1.038 ± 0.015 Å; O=N=O, 121.4 ± 0.5°; O=N-C, 119.3 ± 0.3°; N-C-C, 120.5 ± 0.4°, C1(N)-C2-O, 122.8 ± 0.7°, C-O-H, 116 ± 3°, C6-C1-C2, 119.1 ± 0.7°, C1-C2-C3, 120.4 ± 0.5°; C2-C3-C4, 118.3 ± 0.5°, C3-C4-C5, 123.6 ± 0.6°. © 1993 American Chemical Society.
Добавил в систему:
Borisenko Konstantin B.