Spectroscopic Evidence for Intermolecular Hydrogen Bonds between Phenylacetylene and Various Organic Solvents

Stanford, Spencer C.; Gordy, Walter

doi:10.1021/ja01849a056

Cited by 23 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

Acid-base behavior in aprotic organic solvents

Davis¹

1968

View full text Add to dashboard Cite

Butyl hydroperoxide and deuteroperoxide. Deuterium isotope effects on hydrogen bonding by Br0nsted acids 40 4.3. Hydrogen-bonded ion pairs 41 4.3.1. Conductance 41 a. Walden's work 42 b. Wynne-Jones' postulate 42 c. Investigations of Kraus, Fuoss, and associates... 43 d. Summary 45 4.3.2. Dielectric constants 46 a. Dielectric polarization of substituted ammonium picrates and halides in benzene 46 b. Dielectric polarization of other acid-base complexes in benzene 47 4.3.3. CoUigative properties 49 a. Cryoscopy 50 Page b. The differential vapor pressure (DVP) method... 51 104 4.5.6. Homoconjugation of other organic and inorganic acids a. Perchloric acid 105 b. Other acids 105 4.5.7. Heteroconjugate anions 105 a. Chemical behavior 105 b. Physical measurements 108 4.6. Concluding discussion of hydrogen bonding 112 4.6.1. Definition of a hydrogen bond. Systems which form hydrogen bonds 112 4.6.2! Some recent concepts of hydrogen bonding 113 5. Acidity and basicity scales in aprotic organic solvents... 114 5.1. Early attempts to determine relative acidities 114 5.2. Log Kbha scales of acidity and basicity 115 5.3. Methods used in determining values of log A^bha 116 5.4. Tables of log ^bha, and AS obtained using aprotic solvents 118 5.4.1. Aromatic and substituted aromatic hydrocarbons 118 a. Benzene 118 b. Anisole and chlorobenzene 126 5.4.3. Carbon tetrachloride 126 5.4.4. Chloroform 128 5.4.5. Miscellaneous aprotic solvents 129 6. Acid-base titrations in completely aprotic solvents 133 6.1. Introduction 133 6.2. Titrations with indicator dyes in completely aprotic solvents 133 6.3. Instrumental procedures for detecting end-points in completely aprotic solvents 133 6.3.1. Conductance titrations 133 iv Contents -Continued Page 6.3.2. Dielectrometric titrations 133 6.3.3. Photometric titrations 134 6.3.4. Thermometric titrations 135 6.3.5. Titrations by the DVP method 135 6.3.6. Cryoscopic titrations 135 6.3.7. Other possible instrumental procedures 135 a. Refractive index 135 b. Density 135 c. Optical rotation 135 6.4. Reference acids and bases for aprotic organic solvents 135 6.4.1. Acids 135 a. Hydrogen chloride 135

show abstract

Section: Chci3mentioning

confidence: 95%

Acid-base behavior in aprotic organic solvents

Davis¹

1968

View full text Add to dashboard Cite

show abstract

“…(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 Important Role of Lone-Pairs in Force Field (MM4) Calculations on Hydrogen Bonding in Alcohols

Lii

Allinger

2008

J. Phys. Chem. A

View full text Add to dashboard Cite

An expanded treatment of hydrogen bonding has been developed for MM4 force field calculations, which is an extension from the traditional van der Waals-electrostatic model. It adds explicit hydrogen-bond angularity by the inclusion of lone-pair directionality. The vectors that account for this directionality are placed along the hydrogen acceptor and its chemically intuitive electron pairs. No physical lone-pairs are used in the calculations. Instead, an H-bond angularity function, and a lone-pair directionality function, are incorporated into the hydrogen-bond term. The inclusion of the lone-pair directionality results in improved accuracy in hydrogen-bonded geometries and interaction energies. In this work is described hydrogen bonding in alcohols, and also in water and hydrogen fluoride dimer. The extension to other compounds such as aldehydes, ketones, amides, and so on is straightforward and will be discussed in future work. The conformational energies of ethylene glycol are discussed.

show abstract

“…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%