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Titolo:
EFFECT OF INTERMOLECULAR O-H-CENTER-DOT-CENTER-DOT-CENTER-DOT-O HYDROGEN-BONDING ON THE MOLECULAR-STRUCTURE OF PHENOL - AN AB-INITIO MOLECULAR-ORBITAL STUDY
Autore:
RAMONDO F; BENCIVENNI L; PORTALONE G; DOMENICANO A;
Indirizzi:
UNIV LAQUILA,DEPT CHEM CHEM ENGN & MAT I-67100 LAQUILA ITALY UNIV LAQUILA,DEPT CHEM CHEM ENGN & MAT I-67100 LAQUILA ITALY UNIV ROMA LA SAPIENZA,DEPT CHEM I-00185 ROME ITALY
Titolo Testata:
Structural chemistry
fascicolo: 1, volume: 6, anno: 1995,
pagine: 37 - 45
SICI:
1040-0400(1995)6:1<37:EOIOH>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
SUBSTITUTED BENZENE-DERIVATIVES; ELECTRON-DIFFRACTION; CRYSTAL-STRUCTURE; GEOMETRY; RINGS; ENOLS; PHASE;
Keywords:
PHENOL; PHENOL DIMER AND TRIMER; PHENOL WATER COMPLEXES; INTERMOLECULAR HYDROGEN BONDING; BENZENE RING DEFORMATION; GAS-CRYSTAL STRUCTURAL DIFFERENCES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
37
Recensione:
Indirizzi per estratti:
Citazione:
F. Ramondo et al., "EFFECT OF INTERMOLECULAR O-H-CENTER-DOT-CENTER-DOT-CENTER-DOT-O HYDROGEN-BONDING ON THE MOLECULAR-STRUCTURE OF PHENOL - AN AB-INITIO MOLECULAR-ORBITAL STUDY", Structural chemistry, 6(1), 1995, pp. 37-45

Abstract

The effect of intermolecular O-H...O hydrogen bonding an the molecular structure of phenol has been studied by SCF ab initio MO calculations at the HF/6-31G level. The systems investigated are eight phenol-water complexes and the dimer and trimer of phenol. Optimized geometriesshow that hydrogen bond formation causes a consistent pattern of changes in the structure of the molecule. When phenol acts as a proton donor, the expected increase of r(O-H) is accompanied by a slight decrease of r(C-O) and of the internal ring angles at the ipso and para positions, and by an increase of r(C-ipso-C-ortho). These changes suggest that the relative contribution of polar canonical forms to the electronic structure of the molecule increases upon hydrogen bond formation, since this enhances the strength of the interaction. The opposite changes occur when phenol acts as a proton acceptor, except for r(O-H), which is the same as in the free molecule. If phenol acts as a proton donor and as a proton acceptor, the two hydrogen bonds become stronger due to a synergic effect. In this case, however, the structural deformation of the molecule is less pronounced than in the previous cases, dueto the opposite effect of the two hydrogen bonds. The available experimental evidence on gas-crystal structural differences for phenol is critically reviewed, also in the light of the present results on gas-phase complexes.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 24/09/20 alle ore 09:56:58