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Bond order and charge localization in nucleoside phosphorothioates.

P A Frey, R D Sammons

    Science (New York, N.Y.)
    |May 3, 1985
    PubMed
    Summary

    Structural formulas for nucleoside phosphorothioate anions are often depicted incorrectly. Physical data reveal a single P-S bond and localized negative charge on sulfur, contrary to common representations.

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    Area of Science:

    • Chemical structure and bonding
    • Nucleoside chemistry
    • Phosphorus-sulfur compounds

    Background:

    • Current literature often depicts nucleoside phosphorothioate anions with a P=S double bond and a P-O single bond, localizing negative charge on oxygen.
    • This representation contradicts physical evidence regarding the electronic structure of these important biomolecules.

    Purpose of the Study:

    • To re-evaluate the structural and bonding characteristics of nucleoside phosphorothioate anions.
    • To reconcile discrepancies between theoretical representations and experimental physical data.

    Main Methods:

    • Analysis of X-ray crystallographic and electron diffraction data for bond lengths.
    • Nuclear magnetic resonance (NMR) spectroscopy (31P and 17O) to probe electronic environments.
    • Vibrational spectroscopy of thiophosphate anions.
    • Determination of pKa values for related phosphoric and thiophosphoric acids.

    Main Results:

    • Physical data indicate a single P-S bond with negative charge localized on sulfur in phosphorothioate anions.
    • P-O bond orders are greater than 1, approaching 2 in monoanions and dialkyl phosphorothioates.
    • P-O bond orders in phosphorothioate dianions and trianions are approximately 1 1/2 and 1 1/3, respectively, due to charge delocalization.

    Conclusions:

    • The bonding in nucleoside phosphorothioate anions involves a single P-S bond and significant P-O double bond character.
    • Experimental evidence refutes the commonly accepted structural formulas, highlighting the importance of physical data in chemical representation.

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