Basicity and solvent effects on hydrogen bonding in NR3 ⋯ HCOOH (R = H, CH3) model systems

Patricia Pérez, Gerald Zapata-Torres, Julia Parra-Mouchet, Renato Contreras

Resultado de la investigación: Article

7 Citas (Scopus)

Resumen

The effect of the basicity of methyl-amines on hydrogen bonding (HB) with HCOOH is examined in both gas and solution phases. In the gas phase, the strength of HB may be related to the proton affinity (PA) difference between the carboxylate anion and the methyl-amine, ΔPA = PA(HCOO-) - PA(NR3). The changes in the driving potential ΔPA are explained on the basis of electronic substituent effects. The electronic substituent effects are rationalized in terms of local reactivity indices such as the Fukui function and the local hardness and softness at the basic center. A simple model is then proposed to explain the enhancement HB in the solution phase. The HB pattern in the solution phase is changed by electrostatic and nonelectrostatic solvation of the zwitterionic and neutral species in equilibrium.

Idioma originalEnglish
Páginas (desde-hasta)387-394
Número de páginas8
PublicaciónInternational Journal of Quantum Chemistry
Volumen74
N.º4
EstadoPublished - 1999

Huella dactilar

Alkalinity
affinity
Protons
Hydrogen bonds
protons
hydrogen
Amines
amines
Gases
vapor phases
softness
Solvation
electronics
carboxylates
Anions
solvation
Electrostatics
hardness
reactivity
Hardness

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Condensed Matter Physics
  • Atomic and Molecular Physics, and Optics

Citar esto

Pérez, Patricia ; Zapata-Torres, Gerald ; Parra-Mouchet, Julia ; Contreras, Renato. / Basicity and solvent effects on hydrogen bonding in NR3 ⋯ HCOOH (R = H, CH3) model systems. En: International Journal of Quantum Chemistry. 1999 ; Vol. 74, N.º 4. pp. 387-394.
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abstract = "The effect of the basicity of methyl-amines on hydrogen bonding (HB) with HCOOH is examined in both gas and solution phases. In the gas phase, the strength of HB may be related to the proton affinity (PA) difference between the carboxylate anion and the methyl-amine, ΔPA = PA(HCOO-) - PA(NR3). The changes in the driving potential ΔPA are explained on the basis of electronic substituent effects. The electronic substituent effects are rationalized in terms of local reactivity indices such as the Fukui function and the local hardness and softness at the basic center. A simple model is then proposed to explain the enhancement HB in the solution phase. The HB pattern in the solution phase is changed by electrostatic and nonelectrostatic solvation of the zwitterionic and neutral species in equilibrium.",
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Basicity and solvent effects on hydrogen bonding in NR3 ⋯ HCOOH (R = H, CH3) model systems. / Pérez, Patricia; Zapata-Torres, Gerald; Parra-Mouchet, Julia; Contreras, Renato.

En: International Journal of Quantum Chemistry, Vol. 74, N.º 4, 1999, p. 387-394.

Resultado de la investigación: Article

TY - JOUR

T1 - Basicity and solvent effects on hydrogen bonding in NR3 ⋯ HCOOH (R = H, CH3) model systems

AU - Pérez, Patricia

AU - Zapata-Torres, Gerald

AU - Parra-Mouchet, Julia

AU - Contreras, Renato

PY - 1999

Y1 - 1999

N2 - The effect of the basicity of methyl-amines on hydrogen bonding (HB) with HCOOH is examined in both gas and solution phases. In the gas phase, the strength of HB may be related to the proton affinity (PA) difference between the carboxylate anion and the methyl-amine, ΔPA = PA(HCOO-) - PA(NR3). The changes in the driving potential ΔPA are explained on the basis of electronic substituent effects. The electronic substituent effects are rationalized in terms of local reactivity indices such as the Fukui function and the local hardness and softness at the basic center. A simple model is then proposed to explain the enhancement HB in the solution phase. The HB pattern in the solution phase is changed by electrostatic and nonelectrostatic solvation of the zwitterionic and neutral species in equilibrium.

AB - The effect of the basicity of methyl-amines on hydrogen bonding (HB) with HCOOH is examined in both gas and solution phases. In the gas phase, the strength of HB may be related to the proton affinity (PA) difference between the carboxylate anion and the methyl-amine, ΔPA = PA(HCOO-) - PA(NR3). The changes in the driving potential ΔPA are explained on the basis of electronic substituent effects. The electronic substituent effects are rationalized in terms of local reactivity indices such as the Fukui function and the local hardness and softness at the basic center. A simple model is then proposed to explain the enhancement HB in the solution phase. The HB pattern in the solution phase is changed by electrostatic and nonelectrostatic solvation of the zwitterionic and neutral species in equilibrium.

KW - Hydrogen bonding

KW - Proton transfer potentials

KW - Solvent effects

KW - Substituent effects

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M3 - Article

AN - SCOPUS:1842671553

VL - 74

SP - 387

EP - 394

JO - International Journal of Quantum Chemistry

JF - International Journal of Quantum Chemistry

SN - 0020-7608

IS - 4

ER -