Inclusion compounds of l,d-dipeptide with small sulfoxides: flexible sheet structure of (S)-phenylglycyl-(R)-phenylglycine

Akazome, Motohiro; Hirabayashi, Atsushi; Senda, Kyoko; Ogura, Katsuyuki

doi:10.1016/j.tet.2007.07.061

Cited by 10 publications

(4 citation statements)

References 37 publications

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“…Several studies on the geometrical characteristics [ 62 , 63 ] and the structural effects of these interactions have been published [ 64 , 65 , 66 , 67 ]. Together with other authors Nishio proposed that these C-H⋯π interactions were the result mainly of dispersion forces, particularly where the donor carbon atom presented sp 3 or sp 2 hybridization [ 64 , 68 ].…”

Section: Introductionmentioning

confidence: 99%

Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes

Shimizu

Silva

2018

Molecules

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This paper focuses in the influence of halogen atoms in the design and structural control of the crystal packing of Group VIII halogenated metallocenes. The study is based on the present knowledge on new types of intermolecular contacts such as halogen (X⋯X, C-X⋯H, C-X⋯π), π⋯π, and C-H⋯π interactions. The presence of novel C-H⋯M interactions is also discussed. Crystal packings are analysed after database search on this family of compounds. Results are supported by ab initio calculations on electrostatic charge distributions; Hirshfeld analysis is also used to predict the types of contacts to be expected in the molecules. Special attention is given to the competition among hydrogen and halogen interactions, mainly its influence on the nature and geometric orientations of the different supramolecular motifs. Supramolecular arrangements of halogenated metallocenes and Group IV di-halogenated bent metallocenes are also compared and discussed. Analysis supports halogen bonds as the predominant interactions in defining the crystal packing of bromine and iodine 1,1′-halometallocenes.

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Section: Introductionmentioning

confidence: 99%

Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes

Shimizu

Silva

2018

Molecules

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“…8 Consequently, the hydrogens a to the sulfur moiety are well positioned to act as hydrogen bond donors. Despite a CSD review on sulfoxides, 9 examples of DMSO co-crystals, 10 sulfoxide inclusions 11 and p-haloaryl sulfoxides 12 little is known about the robustness of a-methylene sulfoxides as hydrogen bond donors in crystal engineering. We previously reported investigation of crystal engineering involving sulfoxides, including exploration of competition between hydrogens adjacent to a sulfinyl group and terminal alkynes as hydrogen bond donors.…”

Section: Introductionmentioning

confidence: 99%

Does intermolecular SO⋯H–C–SO hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?

et al. 2010

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“…(1) Formation of a third C(8) chain. This has been observed for (S)-fGly-(R)-fGly (Akazome et al, 2007), but with l-l chirality only for the non-layered structures of Ala-Ala (Fletterick et al, 1971) and two other dipeptides with small side chains (see Table S3 in the supporting information).…”

Section: Resultsmentioning

confidence: 66%

Hydrophobic dipeptides: the final piece in the puzzle

Görbitz

2018

Acta Crystallogr Sect B

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The crystal structure of L-valyl-L-leucine acetonitrile solvate presented here adds to 24 previously reported structures of dipeptides constructed from the five nonpolar amino acids L-alanine, L-valine, L-isoleucine, L-leucine and L-phenylalanine. It thus constitutes the final piece in the 5 × 5 puzzle of hydrophobic dipeptide structures. This opportunity is taken to review the crystal packing arrangements and hydrogen-bonding preferences of a rather unique group of substances, with updated information on the various hydrogen-bonding patterns and the associated peptide conformations.

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Inclusion compounds of l,d-dipeptide with small sulfoxides: flexible sheet structure of (S)-phenylglycyl-(R)-phenylglycine

Cited by 10 publications

References 37 publications

Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes

Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes

Does intermolecular SO⋯H–C–SO hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?

Hydrophobic dipeptides: the final piece in the puzzle

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