Studies of Hydrogen Bonding. Part III. Intermolecular Hydrogen Bond Association between Nitrogen Compounds and Methanol, Phenol, alpha-Naphthol and Pentachlorophenol.

Gramstad, Thor; Snaprud, Svein Ivar; Salmenperä, A.; Block-Bolten, A.; Toguri, J. M.; Flood, H.

doi:10.3891/acta.chem.scand.16-0807

Cited by 98 publications

(21 citation statements)

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“…As can be seen from Fig. 2 there is a correlation between the fractionation factor and hydrogen bonding energy (15,18,19). An especially good correlation is found between the fractionation factor and the Reichardt ET parameters (20) (Fig.…”

Section: Figmentioning

confidence: 69%

“…For MA, on the other hand, the OH group interacts with the T-electrons of C2C14 and C6H6 and interacts via O-H ... 0 and O-H ... N hydrogen bonds with (CH,),O, C5H5N, and CH,CN. These interaction energies (6,(15)(16)(17)(18)(19) and, consequently, the solvation energies differ greatly and this should affect the observed fractionation factor. As can be seen from Fig.…”

Section: Figmentioning

confidence: 99%

See 1 more Smart Citation

Hydrogen isotope fractionation between methanol and diphenylphosphine or dimethylphosphine in the gas phase and in aprotic solvents

Wawer¹,

Szydtlowski²

1996

Can. J. Chem.

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DIH fractionation factors between MeOH and Ph2PH in dilute solutions of tetrachloroethylene, benzene, tetrahydrofuran, pyridine, and acetonitrile and TM fractionation factors between MeOH and Me,PH vapors were measured. The experimental results agree very well with values calculated from the statistical theory of isotope effects formulated by Bigeleisen and Mayer. There are correlations between observed fractionation factors and solvent polarity, and the interaction energy of methanol with the given solvent. Another correlation has been found between enthalpy of the exchange reactions and the interaction energy between methanol and the given solvent.

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Section: Figmentioning

confidence: 69%

Section: Figmentioning

confidence: 99%

Hydrogen isotope fractionation between methanol and diphenylphosphine or dimethylphosphine in the gas phase and in aprotic solvents

Wawer¹,

Szydtlowski²

1996

Can. J. Chem.

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“…were determined mostly by Gramstad and co-workers [49][50][51][52][53][54][55][56][57][58][59] in Norway, mainly between 1960 and 1969, using a near-infrared (NIR) spectroscopic method. This method employs the first overtone of the stretching O H vibration of phenol at 7052 cm −1 (1418 nm).…”

Section: Hydrogen-bond Basicity Scales: Early Workmentioning

confidence: 99%

Thermodynamic and Spectroscopic Scales of Hydrogen‐Bond Basicity and Affinity

2009

Lewis Basicity and Affinity Scales

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Water, alcohols, phenols, hydrogen halides, carboxylic acids, primary and secondary amines and amides, thiols, 1-alkynes and so on constitute a special class of Lewis acids. They all contain an XH group in which the hydrogen atom is bonded to an electronegative atom X and bears a partial positive charge. Therefore, the hydrogen is attracted, by means of electrostatic forces, toward high electron density regions, mainly the lone pairs of Lewis bases B, and a hydrogen bond (HB) X H · · · B is formed. In addition to this electrostatic interaction, there is a charge transfer from the base to the antibonding orbital σ * of the X H sigma bond. The respective contributions of electrostatic forces and charge transfer are a matter of debate. A modern electrostatic model of the hydrogen bond provides a near-quantitative description of structure and properties for a wide range of typical hydrogen bonds [1]. In contrast, NBO analysis suggests that charge transfer of n→σ * type is a characteristic feature of hydrogen bonding [2,3]. In any case, the existence of even a small charge transfer allows the hydrogen-bonding interaction to be considered as Lewis acid/base in nature [4]. The hydrogen-bond donor (HBD) XH is the electron acceptor and the hydrogen-bond acceptor (HBA) B is the electron donor. In the HSAB concept, HBDs are classified as hard Lewis acids [4] from the simple observation that the hydrogen bond is stronger when B is fluorine, oxygen or nitrogen than when it is iodine, sulfur or phosphorus, respectively.The reaction 4.1 of formation of a hydrogen bond between the molecules XH and B:can be used for the construction of a Lewis basicity scale, if a reference HBD is chosen and if the equilibrium constant K of the reaction is measured for a series of bases B under the same conditions: physical state (gas or solution in a given solvent), temperature and pressure. Such a scale, as logK or ∆G, must be named a hydrogen-bond basicity scale.

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“…However, Gramstad [130] has tabulated AvOH, AH, K and Mvalues for the association of phenol, methanol and IX-naphthol with a variety of tertiary bases. It is therefore easier to study associations to nitrogen with less active donors, such as chloroform or phenyl acetylene.…”

Section: Oh N Systemsmentioning

confidence: 99%

Associated XH Frequencies, the Hydrogen Bond

Bellamy¹

1980

The Infrared Spectra of Complex Molecules

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Studies of Hydrogen Bonding. Part III. Intermolecular Hydrogen Bond Association between Nitrogen Compounds and Methanol, Phenol, alpha-Naphthol and Pentachlorophenol.

Cited by 98 publications

References 0 publications

Hydrogen isotope fractionation between methanol and diphenylphosphine or dimethylphosphine in the gas phase and in aprotic solvents

Hydrogen isotope fractionation between methanol and diphenylphosphine or dimethylphosphine in the gas phase and in aprotic solvents

Thermodynamic and Spectroscopic Scales of Hydrogen‐Bond Basicity and Affinity

Associated XH Frequencies, the Hydrogen Bond

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