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Ab initio calculations, including natural charge population and natural resonance theory analyses, have been carried out to study the two-way effects between hydrogen bonds (H-bonds) and the intramolecular resonance effect by using the H-bonded complexes of ring compounds containing the H2N-C=Y moiety (C=Y bond is contained in the six-membered or five-membered rings) with water as models. The amino groups in the four monomers of ring compounds (FAYs, Y represents the heavy atoms in the substituent groups, =CH, =N, =SiH, and =P, respectively) can all serve as H-bond donors (HD) and H-bond acceptors (HA) to form stable H-bonded complexes with water. The HD H-bond and resonance effect enhance each other (positive two-way effects) whereas the HA H-bond and resonance effect weaken each other (negative two-way effects). The resonance effect in FAY(1) (C=Y bond is contained in the six-membered rings) is weaker than that in formamide, and those in FAY(2) and FAY(3) (C=Y bonds are contained in the five-membered rings). The two-way effects between H-bond and resonance effect exist in the H-bonded complexes of ring compounds containing the H2N-C=Y moiety with water.

Ab initio study of hydrogen bond complexes of ring compounds containing the H2N-C=Y moiety with water