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|a eng
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| 100 |
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|a Yamabe, Shinichi
|e verfasserin
|4 aut
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|a A computational study of interactions between acetic acid and water molecules
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|c 2003
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|a Text
|b txt
|2 rdacontent
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|a ohne Hilfsmittel zu benutzen
|b n
|2 rdamedia
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|a Band
|b nc
|2 rdacarrier
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|a Date Completed 09.12.2003
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|a Date Revised 29.04.2003
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|a published: Print
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|a Citation Status PubMed-not-MEDLINE
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|a Copyright 2003 Wiley Periodicals, Inc. J Comput Chem 24: 939-947, 2003
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|a Density functional theory calculations were performed for the title reactions to elucidate the difference between the strong cyclic hydrogen bond of (Me-COOH)(2) and the electrolytic dissociation, MeCOOH <==> Me-COO(-) + H(+), as a weak acid. The association of water clusters with acetic acid dimers strengthens the cyclic hydrogen bond. A nucleophilic attack of the carboxylic carbon by a water cluster leads to a first zwitterionic intermediate, MeCOO(-) + H(3)O(+) + (HO)(3)C-Me. The intermediate is unstable and is isomerized to a neutral interacting system, MeCOOH...(HO)(3)C-Me + H(2)O. The ethanetriol, (HO)(3)-CMe is transformed to an acetic acid monomer. The monomer may be dissociated to give a second zwitterionic intermediate with reasonable proton-relay patterns and energy changes. In proton relay reaction channels, H in MeCOOH is not an acidic proton but is always a hydroxy proton
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|a Journal Article
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|a Tsuchida, Noriko
|e verfasserin
|4 aut
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|i Enthalten in
|t Journal of computational chemistry
|d 1984
|g 24(2003), 8 vom: 30. Juni, Seite 939-47
|w (DE-627)NLM098138448
|x 0192-8651
|7 nnns
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|g volume:24
|g year:2003
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|g day:30
|g month:06
|g pages:939-47
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