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Hydrogen bonding interaction between 1-octylthymine (1) and 9-octyladenine (2) was analyzed by dynamic proton NMR spectroscopy. A mathematical model that takes into account the independent self-association of 1 and 2 was developed in order to determine the equilibrium constant of the interaction between 1-octylthymine and 9-octyladenine K1-2. The measurement of K1-2, in CDCl3, in the range of temperatures of –30 to 40 o C permitted estimation of the contributions of enthalpy ∆H o = –6.74 kcal/mol, and entropy ∆S o = – 13.95 cal mol -1 K -1 , to the hetero-association process. From the enthalpic point of view the association of 1-octylthymine with 9-octyladenine is 0.56 kcal/mol stronger than the self-association of 1octylthymine, and 0.09 kcal/mol stronger than the self-association of 9-octyladenine. X-ray diffraction of a monocrystal of mixed 1-octylthymine and 9-octyladenine indicated that the interaction between these nucleobases in the solid state resemble Haschemeyer-Sobell more than Watson-Crick hydrogen bonding.

Enthalpy and entropy contributions to the equilibrium of the hydrogen bonding interaction between 1-octylthymine and 9-octyladenine