Synthesis and crystal structure of the N-8-(diphenyl-hydroxy-2-aminomethylpyridine)borane, Noemí Andrade-López,*, José G. Alvarado-Rodríguez, Benito Flores-Chávez, Journal of Chemical Crystallography, 35, No. 3, 2005, 191-196. ISSN: 1074-1542 (print version)ISSN: 1572-8854 (electronic version). DOI: 10.1007/s10870-005-2956-3
Reaction of 2-aminomethylpyridine with diphenylborinic acid in a mixture of CHCl3-diethyl ether gives diphenyl-(2-aminomethylpyridine-N,N)borane, a cyclic adduct that in presence of environmental moisture yields the N-8-(diphenyl-hydroxy-2-aminomethylpyridine)borane. The two compounds were characterized by NMR and infrared spectroscopy. The structure of N-8-(diphenyl-hydroxy-2-aminomethylpyridine)borane was confirmed by X-ray diffraction. This adduct crystallizes in monoclinic P21/n space group with unit cell dimensions: a = 13.193(2) (Å), b = 5.913(7) (Å), c = 19.604(2) (Å), = 90.295(3), V = 1529.3(3) Å3, Z = 4. The BN distance is 1.645(3) Å and lies in the range of a dative bond. The NH and OH groups are involved in intermolecular hydrogen bonds formation and they add to the stabilization of the acyclic adduct in the solid state.