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Conformation and Electronic Aspects of Chlor promazine in Solution

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Modern Bioelectrochemistry

Abstract

High-resolution proton and carbon-13 nuclear magnetic resonance spectroscopy studies have been carried out on chlorpromazine base and hydrochloride, and related phenothiazine analogs. Complete unambiguous assignments were possible after the analysis of long-range spin-spin coupling, application of selective heteronuclear and homonuclear decoupling, and ultraviolet irradiation experiments. Negative stain electron micrographs of chlorpromazine hydrochloride showed aggregation of the micelles in water which were shown by NMR analysis to have gauche—trans side-chain conformation in water and chloroform. Selective proton line broadening was observed in chlorpromazine hydrochloride micelles upon ultraviolet irradiation. These results were consistent with a stair-case-like stack of the aggregate in which the ring nitrogen of one molecule interacts with the aromatic ring of the next; the side chains of contiguous molecules orienting in the same direction. In water, the phenothiazine portions of two stacks attract each other so that the side chains extend towards the outside of the micelle. A rationale is adduced for the gauche—trans conformation of the side chain based on the mutual repulsion of the aromatic protons adjacent to the ring nitrogen and the side-chain protons. In chloroform, aggregates are completed by joining two stacks of chlorpromazine hydrochloride via the lyophobic quaternary amines. A possible orientation for the iodine molecule in the chlorpromazine hydrochloride is discussed.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, California State University, Los Angeles, 5151, State University Drive, Los Angeles, California, 90032, USA

    Phoebe K. Dea & Hendrik Keyzer

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  1. Phoebe K. Dea
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  2. Hendrik Keyzer
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Editors and Affiliations

  1. School of Chemistry, Macquarie University, North Ryde, New South Wales, 2113, Australia

    Felix Gutmann

  2. Department of Chemistry and Biochemistry, California State University, 5151 State University Drive, Los Angeles, California, 90032, USA

    Hendrik Keyzer

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© 1986 Plenum Press, New York

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Dea, P.K., Keyzer, H. (1986). Conformation and Electronic Aspects of Chlor promazine in Solution. In: Gutmann, F., Keyzer, H. (eds) Modern Bioelectrochemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2105-7_18

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  • DOI: https://doi.org/10.1007/978-1-4613-2105-7_18

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-9246-3

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