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N–H•••O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters

Crystal and molecular structures of three aminophosphonate diesters, diethyl and dibutyl [alpha-(quinolin-3-ylamino)-N-benzyl]phosphonates (1 and 2) and dibutyl [alpha-anilino-(quinolin-3-yl)methyl]phosphonate (3) were reported and comparatively discussed. Characteristic structural feature for these compounds are strong N–H•••O=P hydrogen bonds that connect two organophosphorus molecules in cyclic centrosymmetric dimer. Phosphoryl oxygen forms additional interaction with a C–H donor from the nearby aromatic group. Dimer formation in solution was also confirmed using electrospray ionization mass spectrometry. Mass spectra of six structurally similar aminophosphonate derivatives, 1-3 along with diethyl [alpha-anilino-(quinolin-3-yl)methyl]phosphonate (4), diethyl and dibutyl [alpha-anilino-(quinolin-2-yl)methyl]phosphonates (5 and 6) were studied and dimolecular ions [2M+Na]+ and [2M+H]+ were observed.

aminophosphonate; hydrogen-bonded dimers; X-ray structure analysis; ESI mass spectrometry

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