Solvent effects in u.v. absorption spectra. IV. Substituted phenols,anisole and phenetole |
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| Affiliation: | 1. Chemistry Department, The University of Jordan, Amman 11942, Jordan;2. Chemistry Department, Tafila Technical University, Tafila 66110, Jordan;3. Technische Universität Chemnitz, Faculty of Natural Sciences, Institute of Chemistry, Inorganic Chemistry, D-09107 Chemnitz, Germany;1. Instituto Tecnológico da Aeronáutica, Praça Marechal Eduardo Gomes, 12228-900 São José dos Campos, SP, Brazil;2. Instituto Federal de Educação, Ciência e Tecnologia de São Paulo, Rodovia Presidente Dutra km 145 - Jardim Diamante, 12223-201 São José dos Campos, SP, Brazil;3. Instituto de Estudos Avançados, Trevo Coronel Aviador José Alberto Albano do Amarante 01 - Putim, SP, 12228-001 São José dos Campos, SP, Brazil;4. Instituto da Aeronáutica e Espaço, Laboratório de Caracterização Físico-Química, Divisão de Materiais, Praça Marechal Eduardo Gomes, 12228-904 São José dos Campos, SP, Brazil;5. Universidade do Estado de Santa Catarina, Centro de Ciências Tecnológicas, Rua Paulo Malschitzki, 200 - 89219-710, Joinville, SC, Brazil;1. Department of Physics, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan;2. Kanazawa University, Kakuma, Kanazawa, 920-1192, Japan;1. Department of Physics, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan;2. Kanazawa University, Kakuma, Kanazawa 920-1192, Japan |
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| Abstract: | The u.v. absorption spectra of some substituted phenols, mostly with the substituents in the ortho positions, have been measured in mixtures of cyclohexane and ethanol and, in some cases, in mixtures of cyclohexane and alternative hydrogen bonding solvents. The loss of the vibrational fine structure has been used as a measure of the ability of the solute molecules to form hydrogen bonds. The behaviour of o-isopropyl phenol does not differ significantly from that of phenol; hence the isopropyl group does not produce hindering to hydrogen bonding. A detectable degree of hindering occurs with 2,6-xylenol and 2,6-dichlorophenol. The vibrational structure of the latter does not disappear completely in ethanol and this is the result of intramolecular bonding between the chlorine atoms and the hydroxyl group. Although 3,5-dichlorophenol is comparable in bonding behaviour to phenol some residual band structure is present even in very strongly associative solvents; possible explanations are discussed. Anisole and phenetole associate rather weakly with ethanol and this is confirmed by the measurement of the shift in the hydroxyl stretching frequency in the i.r. spectrum. This result is interpreted in terms of a marked delocalisation of the ether oxygen lone-pair electrons. |
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