Substituent effects on weakly bound complexes of phenols and carbon monoxide in argon matrices: hydrogen bonding at cryogenic temperatures
Quenching at 20 K of gaseous mixtures consisting of argon, a monosubstituted phenol, and carbon monoxide (M:R:CO = 500:1:5) leads to complexes which have nu/sub OH/ and nu/sub CO/ stretching frequencies shifted 28-60 and 10-16.5 cm/sup -1/, respectively, from monomeric values. The magnitude and direction of shifts involving meta- and para-substituted phenols are consistent with a hydrogen-bound dimer (ArOH...CO) as proposed for the parent phenol. In argon matrices containing ortho-substituted phenols doped with CO, 1:1 complexes are also formed which most likely possess bifurcated hydrogen bonds. For para- and meta-substituted phenols the evidence indicates that the acidity of the phenol is a major factor in inducing shifts of nu/sub OH/ and nu/sub CO/. The shifts induced by ortho-substituted phenols do not correlate well with known aqueous acidities. Speculation thus centers about the role of intrinsic acidities in determining the properties of proton donors in rare-gas matrices. This work represents the first study devoted to substituent effects in gas matrices. 36 references, 7 figures, 2 tables.
- Research Organization:
- State Univ. of New York, Stony Brook
- OSTI ID:
- 5768221
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 106:26; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ABSORPTION SPECTROSCOPY
ARGON
AROMATICS
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CHALCOGENIDES
CHEMICAL REACTIONS
COMPLEXOMETRY
DATA
DISPERSIONS
ELEMENTS
EXPERIMENTAL DATA
FLUIDS
GASES
HYDROXY COMPOUNDS
INFORMATION
INFRARED SPECTRA
MATRIX ISOLATION
MIXTURES
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PHENOLS
RARE GASES
SPECTRA
SPECTROSCOPY
STRUCTURAL CHEMICAL ANALYSIS
VERY LOW TEMPERATURE