VERY STRONG HYDROGEN BONDING OF PHOSPHATES: X-RAY CRYSTAL STRUCTURES OF 1,2,3-BENZOTRIAZOLIUM DIHYDROGEN PHOSPHATE [C₆H₄N₃H₂⁺][H₂PO⁻₄] AND 1,3-BENZIMIDAZOLIUM DIHYDROGEN PHOSPHATE [C₇H₅N₂H₂⁺][H₂PO⁻₄]

John Emsley Department of Chemistry, King's College, Strand, London, WC2R 2LS

Naser M. Reza Department of Chemistry, King's College, Strand, London, WC2R 2LS

Helen M. Dawes Department of Chemistry, Queen Mary College, Mile End Road, London, EI, 4NS

Michael B. Hursthouse Department of Chemistry, Queen Mary College, Mile End Road, London, EI, 4NS

Reiko Kuroda Department of Chemistry, College of General Education, University of Tokyo, Komaba Meguro-ku, Tokyo, 153, Japan

Abstract

1,2,3-Benzotriazole and 1,3-benzimidazole produce crystals of 1:1 adducts with H₃PO₄. Their X-ray structures reveal chains of phosphate ions linked through very short OHO hydrogen bonds. These chains are cross-linked through NHO hydrogen bonds to the 1,3-nitrogen atoms of the protonated bases. Although structurally similar, there are differences between the two systems–the ben-zotriazolium salt having shorter hydrogen bonds than the benzimidazolium salt. This is attributed not to their relvative basicities, but to crystal packing forces.

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VERY STRONG HYDROGEN BONDING OF PHOSPHATES: X-RAY CRYSTAL STRUCTURES OF 1,2,3-BENZOTRIAZOLIUM DIHYDROGEN PHOSPHATE [C₆H₄N₃H₂⁺][H₂PO⁻₄] AND 1,3-BENZIMIDAZOLIUM DIHYDROGEN PHOSPHATE [C₇H₅N₂H₂⁺][H₂PO⁻₄]

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VERY STRONG HYDROGEN BONDING OF PHOSPHATES: X-RAY CRYSTAL STRUCTURES OF 1,2,3-BENZOTRIAZOLIUM DIHYDROGEN PHOSPHATE [C6H4N3H2+][H2PO−4] AND 1,3-BENZIMIDAZOLIUM DIHYDROGEN PHOSPHATE [C7H5N2H2+][H2PO−4]

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VERY STRONG HYDROGEN BONDING OF PHOSPHATES: X-RAY CRYSTAL STRUCTURES OF 1,2,3-BENZOTRIAZOLIUM DIHYDROGEN PHOSPHATE [C₆H₄N₃H₂⁺][H₂PO⁻₄] AND 1,3-BENZIMIDAZOLIUM DIHYDROGEN PHOSPHATE [C₇H₅N₂H₂⁺][H₂PO⁻₄]