Singh, Anil K. ; Sandorfy, Camille ; Fendler, Janos H. (1990) Retinylidene Schiff bases in surfactant-solubilized water pools in heptane Canadian Journal of Chemistry / Revue Canadienne de Chimie, 68 (9). pp. 1514-1522. ISSN 0008-4042
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Official URL: http://www.nrcresearchpress.com/doi/abs/10.1139/v9...
Related URL: http://dx.doi.org/10.1139/v90-233
Abstract
All-trans-retinal (1) was reacted with n-butylamine in sodium bis(2-ethylhexyl)sulfosuccinate (AOT) reverse micelles in heptane to form all-trans-N-retinylidene-n-butylamine Schiff bases (2). The extent of protonation of 2 by 3-chloropropionic acid (CPA) to give 3 in AOT reverse micelles in heptane was found to depend on the ratio of [CPA] to [2], as well as on [H2O]/[AOT] (i.e., on the ω value). At any given [2] and ω values, increasing amounts of CPA increased the protonation and at any given constant [2] and [CPA], increasing ω values also increased the protonation. Over a period of 24 hours, there was only 4% decomposition of 2 in AOT reverse micelles in heptane at ω = 24. Conversely, in three hours, 23% of 3 decomposed in the same system. The trans to cis photoisomerization of 2 in heptane occurred at a much faster rate in the presence of AOT reverse micelles than in their absence. The appearance of carboxylate peaks (FTIR, 1400-1500 cm−1) indicated that the larger the AOT solubilized water pools, the greater the CPA dissociation. 1 also reacted with the α-NH2 group of l-lysine (4) in AOT reverse micelles in heptane to give the corresponding Schiff base 6. Protonation of 6 occurred either intramolecularly or by reaction with unreacted 4. These results were discussed in terms of rhodopsin protonations.
Item Type: | Article |
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Source: | Copyright of this article belongs to NRC Research Press. |
Keywords: | Retinylidene Schiff Bases; Reverse Micelles; Protonation of Schiff Bases; Trans to Cis Photoisomerization |
ID Code: | 72109 |
Deposited On: | 28 Nov 2011 06:03 |
Last Modified: | 28 Nov 2011 06:03 |
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