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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Mizuno, Kazuko Takagi, Tomoko Ikeda, Yohko Shindo, Yohji |
| Copyright Year | 1989 |
| Abstract | The effects of 2-chloroethanol (ClEtOH) on the self-association of three N-acetyl-L-amino acid N′,N′-dimethylamides (Val, Leu, Phe as amino acids) have been studied in water–deuterium oxide solutions by 1H and 13C F.t.n.m.r. These amides were found to self-associate through hydrogen bonding to a small extent. Hydrogen-bonding association of the amides takes place when [ClEtOH]/[amide] > 1. The hydroxyl proton peak of water–ClEtOH mixtures shifts to high field regardless of the presence of the amide owing to the disruption of water structure by ClEtOH. The decrease in the hydrogen-bonding capability of the solvent leads to the hydrogen-bonding association of the amide and ClEtOH induces the hydrogen-bonding association of the amides by decreasing the hydrogen-bonding capability of the solvent around the amides.An apparent dissociation of the amide complexes was found to occur at low concentrations of ClEtOH. This is attributed to the hydrophobic interaction between ClEtOH and the alkyl part of the amides to minimize the energy loss due to the disruption of water structure, and the interaction results in a further decrease in the hydrogen-bonding capability of the solvent around the amides and leads to the start of hydrogen-bonding association of the amides. |
| Starting Page | 1099 |
| Ending Page | 1110 |
| Page Count | 12 |
| File Format | |
| ISSN | 03009599 |
| Volume Number | 85 |
| Issue Number | 5 |
| Journal | Journal of the Chemical Society, Faraday Transactions 1 |
| DOI | 10.1039/F19898501099 |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | Val Hydroxy group Carboxylic acid Alkyl Hydronium 2-Chloroethanol Amide Dissociative Hydrophobe Phe Solvent Hydrogen bond |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry |
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