Ionic hydrogen bond. 1. Sterically hindered bonds. Solvationand clustering of protonated amines and pyridines

Journal Article · Wed May 18 00:00:00 EDT 1983 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00348a005· OSTI ID:5750116

Meot-Ner, M ^[1]; Sieck, L W

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1. Mautner

Using a pulsed high-pressure mass spectrometer, the hydrogen-bonded dimer ions BH/sup +/.B and monohydrates BH/sup +/.H/sub 2/O of 2-alkylpyridines, 2,6-dialkylpyridines, and tertiary amines were investigated in the gas phase in the absence of solvent effects. Steric hindrance causes major entropy effects unfavorable to dimerization or hydration. As long as a single confirmation exists in which the hydrogen bond can obtain optimal geometry, the bond strength is not weakened by steric crowding. However, steric crowding may result in major entropy effects by the hindrance of internal rotors in dimers and monohydrates. 8 figures, 3 tables.

• Research Organization: National Bureau of Standards, Washington, DC
• OSTI ID: 5750116
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 105:10; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400104 -- Spectral Procedures-- (-1987)
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKANES
AZINES
BIPYRIDINES
DATA
DIMERS
ENTROPY
EXPERIMENTAL DATA
FLUIDS
GASES
HETEROCYCLIC COMPOUNDS
HYDRATES
HYDRATION
HYDROCARBONS
INFORMATION
INTERMOLECULAR FORCES
MASS SPECTRA
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHYSICAL PROPERTIES
PULSE TECHNIQUES
PYRIDINES
SOLVATION
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
THERMODYNAMIC PROPERTIES
TIME DEPENDENCE