1941
DOI: 10.1021/ja01849a056
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Spectroscopic Evidence for Intermolecular Hydrogen Bonds between Phenylacetylene and Various Organic Solvents

Abstract: Recent solubility and heat of mixing experi-ments8 provide evidence that acetylene and phenylacetylene may act as proton donors in the presence of the organic solvents mentioned previously. We have undertaken the researches reported here to ascertain whether electron-donor solvents such as amines and ethers produce in the acetylenic CH of phenylacetylene perturbations

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Cited by 23 publications
(5 citation statements)
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“…Shortly after Copley and HoUey's work, Stanford and Gordy [126] obtained supporting evidence of hydrogen bonding from infrared spectra of phenylacetylene mixed with oxygenor nitrogen-containing solvents (acetone, dioxane, triethyl phosphate, A'^jA^-dimethylacetamide, pyridine, and related bases). Recent investigations, principally by infrared spectroscopy and/or NMR spectroscopy, have yielded much additional evidence of C-H...0 and C-H...N formation in acetylene and related compounds, as well as evidence of C-H bonding to other n-or 7r-electron donors.…”
Section: Chci3mentioning
confidence: 95%
“…Shortly after Copley and HoUey's work, Stanford and Gordy [126] obtained supporting evidence of hydrogen bonding from infrared spectra of phenylacetylene mixed with oxygenor nitrogen-containing solvents (acetone, dioxane, triethyl phosphate, A'^jA^-dimethylacetamide, pyridine, and related bases). Recent investigations, principally by infrared spectroscopy and/or NMR spectroscopy, have yielded much additional evidence of C-H...0 and C-H...N formation in acetylene and related compounds, as well as evidence of C-H bonding to other n-or 7r-electron donors.…”
Section: Chci3mentioning
confidence: 95%
“…(6) The linearity of the A-H • • • B segment tends to increase as the strength of the hydrogen bond increases. (7) The protons of hydrogen-bond donors usually tend to be situated on or near the hybrid lone-pair orbital axes of proton acceptors. (8) The association energy of attraction between the molecules concerned increases substantially.…”
Section: Hydrogen-bond Theory and Modelmentioning
confidence: 99%
“…It is in part the Coulombic interaction of the A−H dipole with the excess electron density (or atomic dipole) at the proton-acceptor atom that forms the hydrogen-bond interaction. The strength of the hydrogen bond formed is believed to be best correlated with acidity of the hydrogen atom and basicity of the atom B, although electrostatic interactions are also important. Unless acidity of the hydrogen and basicity of the acceptor atom are sufficient, any hydrogen bonds formed are usually too weak to be significant.…”
Section: Introductionmentioning
confidence: 99%
“…The hydrogen atoms of the CHR groups may also form bridges to carbonyl oxygen atoms, since there is good evidence for C-• • • 0 bridges in comparable structures (24,28,30,32,34,54,60). This possibility will be discussed below in connection with the structure of collagen.…”
Section: Assumptions and General Principlesmentioning
confidence: 99%