Interaction between Benzene and N-Monosubstituted Amides

Suzuki, Isao; Tsuboi, M.; Shimanouchi, Takehiko; Mizushima, San-iehiro

doi:10.1063/1.1730629

Cited by 13 publications

(2 citation statements)

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“…This interaction was first reported in 1959 by Oki and Imamura from the measurements of the IR spectra of N -benzylaniline and its derivatives . The NH/π interaction was also observed in other systems. − In 1986 Perutz et al reported the NH/π interaction in the hemoglobin-drug complex . The short contact was also found in several proteins. − Fong et al reported that the NH/π interaction is important for the selective binding of receptor protein with neurotransmitter…”

Section: Introductionmentioning

confidence: 81%

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Origin of the Attraction and Directionality of the NH/π Interaction: Comparison with OH/π and CH/π Interactions

et al. 2000

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High-level ab initio calculations were carried out to evaluate the interaction between the π face of benzene and ammonia as a model of NH/π interaction. The intermolecular interaction energy was calculated from the extrapolated MP2 interaction energy at the basis set limit and a CCSD(T) correction term. The calculated interaction energy (-2.22 kcal/mol) is considerably smaller than that of the hydrogen bond between waters. The monodentate complex is slightly more stable than the bidentate and tridentate complexes. The potential energy surface is very flat near the minimum, which shows that the major source of the attraction is a longrange interaction. The HF interaction energy of the monodentate complex (0.13 kcal/mol) is repulsive. The large gain in the attraction by electron correlation correction (-2.36 kcal/mol) indicates that the dispersion interaction is significantly important for the attraction. The electrostatic energy (-1.01 kcal/mol) is also important for the attraction. The benzene-water (OH/π) interaction energy (-3.17 kcal/mol) is larger than the benzeneammonia (NH/π) interaction. The dispersion interaction is again important for the attraction in the benzenewater complex. The attraction in the benzene-ammonia complex is stronger than that in the benzene-methane (CH/π) complex (-1.45 kcal/mol). The amount of electrostatic energy is mainly responsible for the magnitude of the attractions in these three complexes. The directionality for the NH/π and OH/π interactions is mainly controlled by the electrostatic interaction.

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Section: Introductionmentioning

confidence: 81%

“…10 The NH/π interaction was also observed in other systems. [11][12][13][14][15][16] In 1986 Perutz et al reported the NH/π interaction in the hemoglobin-drug complex. 17 The short contact was also found in several proteins.…”

Section: Introductionmentioning

confidence: 99%