Carbon-hydrogen bond dissociation energy in methanol

Cruickshank, F. R.; Benson, Sidney W.

doi:10.1021/j100723a041

Cited by 52 publications

(27 citation statements)

References 2 publications

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“…Whittle and co-workers (9, 10) determined the bond dissociation energies D(H-CH,OH) and D[H-CH(CH,)OH] by photobromination to be 92 and 90 kcal/mol, respectively. Benson and co-workers (11,12) …”

Section: Kinetics Resultsmentioning

confidence: 99%

The Flash Photolysis of Tetraphenyldiphosphine, Triphenylphosphine, and Diphenylphosphine in Alcohols

Wong¹,

Sytnyk²,

Wan³

1971

Can. J. Chem.

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The photochemical reactions of tetraphenyldiphosphine, triphenylphosphine, and diphenylphosphine in alcohol were studied by flash photolysis and product analysis. The primary photochemical process of all three phosphines studied appeared to be the formation of diphenylphosphinyl radicals which subsequently abstract a-H atoms from the solvent alcohol. The relationship between the rate constants of the abstraction and the a-H bond energies of various alcohols was examined.Les reactions photochimiques de la tktraphknyldiphosphine et des di-et triphknylphosphines ont kt6 ttudiks, dans l'alcool, par photolyse "flash" et par analyse des produits. Le processus photochimique prirnaire pour les trois phosphines semble &tre la formation de radicaux diphknylphosphinyles qui arrachent subs6quemment des atomes d'hydrogkne-a de I'alcool utilisk cornrne solvant. Une relation entre les constantes de vitesse d'abstraction et les energies de liaison des hydrogenes-a de divers alcools a etk examink.

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Section: Kinetics Resultsmentioning

confidence: 99%

The Flash Photolysis of Tetraphenyldiphosphine, Triphenylphosphine, and Diphenylphosphine in Alcohols

Wong¹,

Sytnyk²,

Wan³

1971

Can. J. Chem.

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“…Even more problematic is the fact that the actual mechanism of activation is very poorly understood in virtually all reported reactions . Elemental iodine is also redox‐active, and it is well known that iodine forms trace amounts of hydrogen iodide in some solvents . Thus, the actual active compound might be traces of acid.…”

Section: Concept and Scopementioning

confidence: 99%

Halogen Bonding in Organic Synthesis and Organocatalysis

Bulfield

Huber

2016

Chemistry A European J

524

348

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Halogen bonding is a noncovalent interaction similar to hydrogen bonding, which is based on electrophilic halogen substituents. Hydrogen-bonding-based organocatalysis is a well-established strategy which has found numerous applications in recent years. In light of this, halogen bonding has recently been introduced as a key interaction for the design of activators or organocatalysts that is complementary to hydrogen bonding. This Concept features a discussion on the history and electronic origin of halogen bonding, summarizes all relevant examples of its application in organocatalysis, and provides an overview on the use of cationic or polyfluorinated halogen-bond donors in halide abstraction reactions or in the activation of neutral organic substrates.

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“…Reference[64] corrected for newer data[29] of -25.95 for dHY(CH,O).Based on an estimated value of 92.5 for DH"(CH,CHOH-H) yielding dHF(CH,CHOH M -15.8) and CH,kHO-H M 104 [84] yielding dHy(CH,kH--6) w 36.1 kcal mol-l. Based on a value of -12.3 for dH;(C.H,),CH-O [84]. Calculatedfrom A H , w 27.4for (CH,),COH+(CH,),C=O+ H [65] and fromDH"(CH,),CHO-H M 104 [84].…”

mentioning

confidence: 99%

Homopolar‐ and Heteropolar Bond Dissociation Energies and Heats of Formation of Radicals and Ions in the Gas Phase. I. Data on organic molecules

Egger¹,

Cocks

1973

Helvetica Chimica Acta

218

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Prepared froni 4-(2,6,6-trimcthylcyclohex-l-cnyl) -but-3-yn-2-01 acetate by epoxidation followed by lithium aluminium hydridc reduction: NMR. (CDCI,) : 1.04(3H, s). 1.20(3H, s ) , 1.27(311, d, J = ~H z ) , 1.34(3H, s), 4,36(1H, q, ,I = 7 Hz), 5,46(1H, d x d , J = 7HZ, J' -5112) ppni; IR. (liq.): 3350, 1955 cm-l.Summary. The literature data on hcteropolar and homopolar 2-center bond dissociation energies in organic molecules in the gas phase and the corrcsponding heats of formation of radicals and ions havc been critically evaluated. Data for more than 500 bonds are represented in tabular form together with the pertinent literature references.Selected electron affinitics and n-bond dissociation energies have also bccn incorporated. The follow-up paper will discuss some cmpirical general aspects of these data particularly regarding the effect of structure on the bond dissociation energies.

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Carbon-hydrogen bond dissociation energy in methanol

Cited by 52 publications

References 2 publications

The Flash Photolysis of Tetraphenyldiphosphine, Triphenylphosphine, and Diphenylphosphine in Alcohols

The Flash Photolysis of Tetraphenyldiphosphine, Triphenylphosphine, and Diphenylphosphine in Alcohols

Halogen Bonding in Organic Synthesis and Organocatalysis

Homopolar‐ and Heteropolar Bond Dissociation Energies and Heats of Formation of Radicals and Ions in the Gas Phase. I. Data on organic molecules

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