Iterative force-field calculations of cycloundecane, cyclotridecane, and cyclopentadecane

Anet, Frank A. L.; Rawdah, Tarik N.

doi:10.1021/ja00493a004

Cited by 35 publications

(36 citation statements)

References 4 publications

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“…According to the strain energy calculations, there are five low-energy conformations, which are separated by low energy barriers (Fig. 72) [31,47]. Two quinquangular conformations are of the lower energy, while three triangular are of somewhat higher.…”

Section: Cyclotridecanementioning

confidence: 99%

“…Two quinquangular conformations are of the lower energy, while three triangular are of somewhat higher. Based on the calculations [48] and the studies of related systems [46,49] [46,47] to be the lowest energy conformation.…”

Section: Cyclotridecanementioning

confidence: 99%

“…There are five low-energy conformations of cyclopentadecane according to the strain energy calculations [31,47]. All of the low-energy conformations are quinquangular (Fig.…”

Section: Cyclopentadecanementioning

confidence: 99%

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Conformational analysis of cycloalkanes

Dragojlović

2015

ChemTexts

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Conformational analysis is a comparatively new area of organic chemistry that has been developed well after the theories of organic reactions, bonding in organic compounds and stereochemistry. It was only in the second half of twentieth century that its importance was fully recognized and its central role with respect to bonding, reactivity and stability of organic compounds was appreciated. Fundamental concepts of conformational analysis, a deeper discussion of the conformational analysis of small and common rings and an introduction into the conformational analysis of medium and large rings are presented at a level suitable for an introductory organic chemistry course. This discussion aims to provide a better understanding of the complex relationship among different types of strain, while also discussing the factors that determine stability of a particular conformation. Finally, the unique nature of each class of cycloalkanes is explored.

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Section: Cyclotridecanementioning

confidence: 99%

Section: Cyclotridecanementioning

confidence: 99%

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Conformational analysis of cycloalkanes

Dragojlović

2015

ChemTexts

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“…Force-field calculations for cycloundecane have identified six conformations within an energy span of 11 kJ mol-1, with the two lowest-energy conformations, [335] and [12323], being nearly identical in strain energy (Anet & Rawdah, 1978). The NMR spectra of cycloundecane demonstrate conformational exchange in solution down to ca 120 K and this has been interpreted in terms of interconversion of the [335] and [12323] forms and pseudorotation of the former (Anet & Rawdah, 1978).…”

Section: Introductionmentioning

confidence: 99%

Dynamic conformational behaviour of an eleven-membered ring in the solid state. X-ray studies of cycloundecylmethyl 1-naphthylcarbamate at 120 and 293 K

Russell¹,

Sim²

1990

Acta Crystallogr Sect B

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The crystal structure of cycloundecylmethyl 1-naphthylcarbamate is ordered at 120 K and the eleven-membered ring exhibits the [12323] conformation of cycloundecane with C--C(sp3)--C angles enlarged beyond tetrahedral, 112.1-118.4(3) °. The crystal structure is disordered at 293 K in the region occupied by the eleven-membered ring and molecular-mechanics calculations establish that the major component of the conformational mixture has the [335] cycloundecane conformation. X-ray studies at 293 K before and after cooling a crystal to 120 K for ca 120 h confirmed that the order-disorder transformation is reversible. The

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“…The interconversion of these conformations in solution follows the mechanism for the racemization of medium-ring trans cycloalkenes (Newton & Whitham, 1979) and trans lactones (Brown, Chaloner & Martens, 1981). The rotation of double bonds through the rings in unsaturated cyclic hydrocarbons has been studied by force-field calculations and NMR spectroscopy (Anet & Rawdah, 1978) and is expected to be a facile process for an eleven-membered ring in the liquid phase at normal temper/ttures (Shirahama, Osawa & Matsumoto, 1980). …”

Section: Discussionmentioning

confidence: 99%