IR-dip and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-(H2O)1. Observation of π-type and σ-type hydrogen-bonded conformers in the CN site

Kenji Sakota, Norifumi Yamamoto, Kazuhiko Ohashi, Morihisa Saeki, Shunichi Ishiuchi, Makoto Sakai, Masaaki Fujii, Hiroshi Sekiya

Research output: Contribution to journalArticle

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Abstract

The IR-dip spectra and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-water 1: 1 complex have been measured to investigate the effects of the introduction of two substituents into the aromatic ring on the hydrogen-bonding interaction and stable structures of the complex. We have obtained a clear evidence for the observation of three structural isomers by comparing the experimental IR spectra with the theoretical ones. The water molecule is bonded to the NH2 site in isomer I, where the amino group can act as a proton donor and the amino hydrogen is bonded to the oxygen atom of water. Water is bonded to the CN site in isomers II and III. The structure of isomer II is very similar to benzonitrile-(H2O)1, where the water hydrogen is bonded to the cyano nitrogen and the oxygen atom of water is bonded to the ortho hydrogen atom. The water hydrogen is linearly hydrogen-bonded to the cyano nitrogen in isomer III. The intermolecular hydrogen bond in isomer II is σ-type, whereas that in isomer III is π-type. The proton-donor conformer in the NH2 site and the σ-type linear conformer in the CN site have not been observed in the aniline-(H2O)1 and benzonitrile-(H2O)1 complexes, respectively. The observation of three stable structures has been successfully explained by atomic charges on the constituent atoms obtained by natural population analysis.

Original languageEnglish
Pages (from-to)209-219
Number of pages11
JournalChemical Physics
Volume283
Issue number1-2
DOIs
Publication statusPublished - Oct 1 2002

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hole burning
Isomers
Hydrogen
isomers
Water
hydrogen
water
Atoms
Protons
oxygen atoms
Hydrogen bonds
Nitrogen
ortho hydrogen
Oxygen
nitrogen
protons
4-aminobenzonitrile
aniline
hydrogen atoms
hydrogen bonds

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Cite this

IR-dip and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-(H2O)1. Observation of π-type and σ-type hydrogen-bonded conformers in the CN site. / Sakota, Kenji; Yamamoto, Norifumi; Ohashi, Kazuhiko; Saeki, Morihisa; Ishiuchi, Shunichi; Sakai, Makoto; Fujii, Masaaki; Sekiya, Hiroshi.

In: Chemical Physics, Vol. 283, No. 1-2, 01.10.2002, p. 209-219.

Research output: Contribution to journalArticle

Sakota, Kenji ; Yamamoto, Norifumi ; Ohashi, Kazuhiko ; Saeki, Morihisa ; Ishiuchi, Shunichi ; Sakai, Makoto ; Fujii, Masaaki ; Sekiya, Hiroshi. / IR-dip and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-(H2O)1. Observation of π-type and σ-type hydrogen-bonded conformers in the CN site. In: Chemical Physics. 2002 ; Vol. 283, No. 1-2. pp. 209-219.
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abstract = "The IR-dip spectra and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-water 1: 1 complex have been measured to investigate the effects of the introduction of two substituents into the aromatic ring on the hydrogen-bonding interaction and stable structures of the complex. We have obtained a clear evidence for the observation of three structural isomers by comparing the experimental IR spectra with the theoretical ones. The water molecule is bonded to the NH2 site in isomer I, where the amino group can act as a proton donor and the amino hydrogen is bonded to the oxygen atom of water. Water is bonded to the CN site in isomers II and III. The structure of isomer II is very similar to benzonitrile-(H2O)1, where the water hydrogen is bonded to the cyano nitrogen and the oxygen atom of water is bonded to the ortho hydrogen atom. The water hydrogen is linearly hydrogen-bonded to the cyano nitrogen in isomer III. The intermolecular hydrogen bond in isomer II is σ-type, whereas that in isomer III is π-type. The proton-donor conformer in the NH2 site and the σ-type linear conformer in the CN site have not been observed in the aniline-(H2O)1 and benzonitrile-(H2O)1 complexes, respectively. The observation of three stable structures has been successfully explained by atomic charges on the constituent atoms obtained by natural population analysis.",
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T1 - IR-dip and IR-UV hole-burning spectra of jet-cooled 4-aminobenzonitrile-(H2O)1. Observation of π-type and σ-type hydrogen-bonded conformers in the CN site

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AU - Yamamoto, Norifumi

AU - Ohashi, Kazuhiko

AU - Saeki, Morihisa

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AU - Fujii, Masaaki

AU - Sekiya, Hiroshi

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