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Hydrogen bonding: HOC=O···H–N vs. HOC=O···H–C

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Abstract

A chloroform-soluble dipyrrinone, 8,9-bis-(5-carboxypentyl)-2,3-bis-(2-methoxyethoxy)-10H-dipyrrin-1-one, with solubilizing 2-methoxyethoxy β-substituents on the lactam ring and two hexanoic acid groups (one at C(9), the other at C(8) of the pyrrole ring) was synthesized to determine its ability to form intramolecular hydrogen bonds to the lactam unit from either carboxylic acid, whether in the syn-(Z) or anti-(Z) conformation. In the syn-(Z) conformation, such intramolecular hydrogen bonds can also include the pyrrole N–H. In the anti-(Z), intramolecular hydrogen bonds can include the pyrrole C(7)-H. Evidence for both monomer conformations in equilibrium is provided by 1H NMR analyses, which indicate that the syn-(Z) is favored over the anti-(Z) and predict an interconversion barrier of approximately 40 kJ mol−1.

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Acknowledgments

SKD and SD were R.C. Fuson Graduate Fellows. Partial support of this work came from the U.S. National Institutes of Health (HD 17779).

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Authors and Affiliations

  1. Milliken & Company, PO Box 1926, Spartanburg, SC, 29304, USA

    Sanjeev K. Dey & Suchitra Datta

  2. Department of Chemistry, University of Nevada, Reno, NV, 89557-0216, USA

    David A. Lightner

Authors
  1. Sanjeev K. Dey
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  2. Suchitra Datta
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  3. David A. Lightner
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Correspondence to David A. Lightner.

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Dey, S.K., Datta, S. & Lightner, D.A. Hydrogen bonding: HOC=O···H–N vs. HOC=O···H–C. Monatsh Chem 145, 1595–1609 (2014). https://doi.org/10.1007/s00706-014-1257-y

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  • DOI: https://doi.org/10.1007/s00706-014-1257-y

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