Cyclopropane rings as proton-acceptor groups in hydrogen bonding

Joris, L.; Schleyer, Paul von Ragué; Gleiter, Rolf

doi:10.1021/ja01004a022

Cited by 68 publications

(25 citation statements)

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“…This density is clearly visible in the accurate charge-density analyses of Nijveldt & Vos (1988a,b,c). In this paper we extend the studies of Viswamitra et al (1993) and Steiner (1995a,b) to try to locate crystallographic evidence for the N,O--H...cp interactions so clearly identified by Joris, Schleyer & Gleiter (1968).…”

Section: Introductionmentioning

confidence: 87%

“…Spectroscopic evidence for the existence of O,N--H... zr hydrogen bonding to acetylenic, olefinic and aromatic acceptors is well documented (Joris, Schleyer & Gleiter, 1968, and references therein). Recently, Viswamitra, Radhakrishnan, Bandekar & Desiraju (1993) have presented a survey of available crystallographic data and have shown that intermolecular examples of these bonds are clearly observed in crystal structures.…”

Section: Introductionmentioning

confidence: 99%

“…Hydrogenbond cooperativity is observed in extended H...2r(C~C) systems and his calculations indicate bond energies in the range 4.2-9.2 kJ mo1-1 . Joris, Schleyer & Gleiter (1968) also used IR spectroscopy to investigate the ability of cyclopropane rings to accept O--H protons in both intra-and intermolecular interactions. This conjecture was made on the basis, again, of the ethylenic properties of cyclopropane (cp) and the spectroscopic evidence is strongly in favour of O--H...cp interactions.…”

Section: Introductionmentioning

confidence: 99%

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The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings

Allen¹,

Lommerse²,

Hoy³

et al. 1996

Acta Crystallogr Sect B

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Section: Introductionmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings

Allen¹,

Lommerse²,

Hoy³

et al. 1996

Acta Crystallogr Sect B

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“…24 However, gas-phase spectroscopic evidence of H-bonded cyclopropane is rather sparse. [27][28][29] A paradigmatic example is the F-H·cyclopropane complex, in which the HF moiety forms an H-bond to the C-C bond of cyclopropane. 29 In 1-NpOH·cyclopropane, a structure can occur with cyclopropane adsorbed to one face of the naphthalene π-system, giving rise to CH · · · π interactions.…”

Section: Introductionmentioning

confidence: 99%

Accurate dissociation energies of two isomers of the 1-naphthol⋅cyclopropane complex

Maity

Knochenmuss

Holzer

et al. 2016

The Journal of Chemical Physics

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Articles you may be interested inInfluences of the propyl group on the van der Waals structures of 4-propylaniline complexes with one and two argon atoms studied by electronic and cationic spectroscopy J. Chem. Phys. 143, 034308 (2015); 10.1063/1.4927004The weak hydrogen bond in the fluorobenzene-ammonia van der Waals complex: Insights into the effects of electron withdrawing substituents on π versus in-plane bonding J. Chem. Phys. 126, 154319 (2007) The 1-naphthol·cyclopropane intermolecular complex is formed in a supersonic jet and investigated by resonant two-photon ionization (R2PI) spectroscopy, UV holeburning, and stimulated emission pumping (SEP)-R2PI spectroscopy. Two very different structure types are inferred from the vibronic spectra and calculations. In the "edge" isomer, the OH group of 1-naphthol is directed towards a C-C bond of cyclopropane, the two ring planes are perpendicular. In the "face" isomer, the cyclopropane is adsorbed on one of the π-aromatic faces of the 1-naphthol moiety, the ring planes are nearly parallel. Accurate ground-state intermolecular dissociation energies D 0 were measured with the SEP-R2PI technique. The D 0 (S 0 ) of the edge isomer is bracketed as 15.35 ± 0.03 kJ/mol, while that of the face isomer is 16.96 ± 0.12 kJ/mol. The corresponding excited-state dissociation energies D 0 (S 1 ) were evaluated using the respective electronic spectral shifts. Despite the D 0 (S 0 ) difference of 1.6 kJ/mol, both isomers are observed in the jet in similar concentrations, so they must be separated by substantial potential energy barriers. Intermolecular binding energies, D e , and dissociation energies, D 0 , calculated with correlated wave function methods and two dispersion-corrected density-functional methods are evaluated in the context of these results. The density functional calculations suggest that the face isomer is bound solely by dispersion interactions. Binding of the edge isomer is also dominated by dispersion, which makes up two thirds of the total binding energy. Published by AIP Publishing. [http://dx

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“…An examination Of the temperature de-three-rnembered ring has precedence in cyclependence of the n.m.r. spectrum of 3e over the propane-OH interactions (23,24) although these temperature range of -90 to 4-140 "C failed to were not so strong ( A~ = 40 cm-1). Perhaps the detect any significant spectral changes.…”

Section: Ll -Epoxy-5-hydroxy-5h-dibenzo[ad]cyclo-mentioning

confidence: 94%

Derivatives of 1-Phenylphthalan, 2-Methyl-1-phenylisoindoline, and 5H-Dibenzo[a,d]cycloheptene Oxides; Synthesis and Conformational Aspects

Fraser¹,

Renaud²

1971

Can. J. Chem.

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For the purpose of correlation of chemical shifts and geminal coupling constants with stereochemistry a number of compounds of fixed geometry have been synthesized. These include seven 6-substituted 1-phenylphthalans, five 6-substituted 2-methyl-1-phenylisoindolines, and six 2-substituted 5H-dibenzo-[a,d]cycloheptene oxides. The geometrical properties of the three ring systems are discussed and arguments in favor of a quasi-equatorial epoxide substituent in the latter series are supported by n.0.e. measurements.

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Cyclopropane rings as proton-acceptor groups in hydrogen bonding

Cited by 68 publications

References 1 publication

The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings

The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings

Accurate dissociation energies of two isomers of the 1-naphthol⋅cyclopropane complex

Derivatives of 1-Phenylphthalan, 2-Methyl-1-phenylisoindoline, and 5H-Dibenzo[a,d]cycloheptene Oxides; Synthesis and Conformational Aspects

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