Abstract
The conformational isomerism, relative stabilities of isomeric forms, acid–base behavior, and hydrogen bonding of formylphosphinous acid (FPA), an isostere of formohydroxamic acid (FHA) and its tautomer formylphosphine oxide have been analyzed in the present study. Molecular orbital and density functional theory methods in conjunction with 6-31+G* basis set have been employed. The protonation, deprotonation, and hydrogen bonding abilities of FHA and FPA have been compared. FPA has P as preferred site of deprotonation like N in FHA, but they differ in their preferred site of protonation. With similar nature and orientation of H-bond donor and acceptor atoms, stabilization energy of most stable aggregate of FHA with water is 0.99 kcal/mol higher than that of similar aggregate of FPA with water. In addition, FPA is more stable than its corresponding oxide form in gas phase as well as on H-bonding interaction with single water molecule.
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