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Crystal Structures of Analogs of threo-Methylphenidate

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Abstract

The crystal structures of the chloride salts of five analogs of threo-methylphenidate have been obtained. Four of these have different substituents on the phenyl ring while the fifth is the ethyl ester of methylphenidate. All five structures have similar three-dimensional conformations and these are compared with the global minimum obtained by MM2-87 calculations. There is good agreement between the crystal structures and the computed global minimum with the major difference being the presence of a chloride counterion in the crystal structures that prevents the carbonyl oxygen from approaching the equatorial ammonium hydrogen as closely as in the computed global minimum.

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Authors and Affiliations

  1. Pharm-Eco Laboratories, 128 Spring Street, Lexington, Massachusetts, 02173-7800

    Mark Froimowitz & Kuo-Ming Wu

  2. Laboratory for the Structure of Matter, Naval Research Laboratory, Washington D.C, 20375-5341

    Clifford George

  3. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332-0400

    Don VanDerveer, Qing Shi & Howard M. Deutsch

Authors
  1. Mark Froimowitz
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  2. Kuo-Ming Wu
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  3. Clifford George
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  4. Don VanDerveer
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  5. Qing Shi
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  6. Howard M. Deutsch
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Correspondence to Mark Froimowitz.

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Froimowitz, M., Wu, KM., George, C. et al. Crystal Structures of Analogs of threo-Methylphenidate. Structural Chemistry 9, 295–303 (1998). https://doi.org/10.1023/A:1022435131188

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  • DOI: https://doi.org/10.1023/A:1022435131188

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