Homochiral Methyl (2R,3S)-3-Bromo-2-chloro-3-phenylpropanoate

Shaw, J.P.; Tan, Eng Wu; Blackman, Allan G.

doi:10.1107/s0108270194008218

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Cited by 4 publications

(2 citation statements)

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“…The major diastereomer 4 was readily isolated by fractional crystallization from hexane. The structure was confirmed by x-ray crystallography to be 2 R ,3 S . The minor diastereomer was assigned the complementary structure 5 .…”

Section: Resultsmentioning

confidence: 82%

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Shaw

Tan

1996

J. Org. Chem.

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Section: Resultsmentioning

confidence: 82%

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Shaw

Tan

1996

J. Org. Chem.

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“…Close intermolecular contacts occur between Brl and H10(2 -x, y + 1/2, 2 -z) [2.989 (7) A], and 02 and H9(2 -x, y + 1/2, 2 -z) [2.438 (8)A]. A similar regioselective (and stereoselective) bromination of a cinnamate derivative has been reported previously (Shaw, Tan & Blackman, 1995).…”

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confidence: 60%

Homochiral Methyl (S)-2-Benzenesulfonyloxy-4-bromo-4-methylpentanoate

Shaw¹,

Tan²,

Blackman³

1995

Acta Crystallogr C

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Noncovalent Interactions in Crystal Structures: Quantifying Cooperativity in Hydrogen and Halogen Bonds

Grabowski

2017

Intermolecular Interactions in Crystals: Fundamentals of Crystal Engineering

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The cooperativity effects for hydrogen and halogen bonded systems are analyzed; examples of clusters where this phenomenon occurs are presented – the systems analyzed theoretically are compared with examples of the corresponding arrangements occurring in crystal structures. This chapter relates to early studies on this phenomenon and it presents different meanings of the term cooperativity. Distinct indices and measures of the cooperativity are presented in order to quantify this phenomenon. Different classifications of the cooperativity are presented; for example, σ- cooperativity and π-cooperativity are described. For the latter case one can distinguish between intermolecular and intramolecular π-cooperativity. It is justified that for numerous kinds of interactions, the hydrogen and halogen bonds, as well as other interactions classified as σ-hole bonds, the same indices describing the cooperativity may be applied. It is shown that in crystal structures where cooperativity effects are mostly related to the symmetry relations, the situation is very complex since various phenomena related to the term cooperativity may act simultaneously.

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Homochiral Methyl (2R,3S)-3-Bromo-2-chloro-3-phenylpropanoate

Abstract: The stereochemistries at positions 2 and 3 of the title compound, C10H10BrCIO2, have been confirmed by Xray crystal structural analysis. The halogen atoms show an antiperiplanar arrangement.

Cited by 4 publications

References 0 publications

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Homochiral Methyl (S)-2-Benzenesulfonyloxy-4-bromo-4-methylpentanoate

Noncovalent Interactions in Crystal Structures: Quantifying Cooperativity in Hydrogen and Halogen Bonds

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