J. Phys. Org. Chem. 23, 526-535 (2010)

DOI: 10.1002/poc.1636

Double proton transfer in crystals of 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a] pyrimidine (hppH): 13C and 15N CPMAS NMR study of (hppH)2

In this paper, we report an example of intermolecular solid-state proton transfer in the bicyclic guanidine, hppH. A combination of X-ray crystallography, CPMAS NMR (13C and 15N) and theoretical calculations allows us to determine that a double proton transfer takes place in the (hppH)2 dimer with an activation energy of about 50 kJ mol−1. According to the B3LYP/6-311++G(d,p) calculations, the double proton transfer occurs non-symmetrically through a zwitterion.