Hydrogen bond studies. XLIV. Neutron diffraction study of acetic acid

Jönsson, Per-Gunnar

doi:10.1107/s0567740871003224

Cited by 146 publications

(52 citation statements)

References 7 publications

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“…Ac‐ΔAla‐NMe 2 , devoid of this group, associates in sharp contrast to these structures: here, chains of molecules are formed. This important difference is also observed between the solid state interactions of acetic acid molecules (chains) (52–55) and those in other monocarboxylic acids with a larger alkyl/aryl group (cyclic dimers). For saturated dimethyldiamides, despite the conformational variations, some order in their associative pattern can be noted.…”

Section: Discussionmentioning

confidence: 94%

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a

Rzeszotarska

Siodłak

Broda

et al. 2002

The Journal of Peptide Research

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A series of three homologous dimethyldiamides Ac-DeltaAla-NMe2, Ac-L-Ala-NMe2 and Ac-DL-Ala-NMe2 has been synthesized and the structures of these amides determined from single-crystal X-ray diffraction data. To learn more about the conformational preferences of compounds studied, the fully relaxed (phi-psi) conformational energy maps in vacuo (AM1) of Ac-DeltaAla-NMe2 and Ac-L-Ala-NMe2 were obtained, and the calculated minima reoptimized with the DFT/B3LYP/6-31G** method. The crystal-state results have been compared with the literature data. Ac-DeltaAla-NMe2 and other alpha,beta-dehydroamino acid dimethyldiamides, Ac-DeltaXaa-NMe2 adopt the conservative conformation of the torsion angles phi, psi = approximately -45 degrees, approximately 130 degrees, which are located in the high-energy region (region H) of Ramachandran diagram. Ac-L-Ala-NMe2 and Ac-DL-Ala-NMe2, as well as other saturated amino acid dimethylamides Ac-L/DL-Xaa-NMe2, present common peptide structures, and no conformational preferences are observed. Molecular packing of the amides analysed reveals two general hydrogen-bonded motifs. Dehydro and DL-species are paired into centrosymmetric dimers, and L-compounds form catemers. However, Ac-DeltaAla-NMe2 and Ac-DL-Ala-NMe2 constitute exceptions: their molecules also link into catemers.

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Section: Discussionmentioning

confidence: 94%

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a

Rzeszotarska

Siodłak

Broda

et al. 2002

The Journal of Peptide Research

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“…Acetic acid can also bind to the CHCO2H moiety of cinnamoylalanine via a cyclic dimer (2c) on the (010) face. The dimer (2b) is the motif adopted by acetic acid in its own crystal structure (Jonsson, 1971), forming a CmH-..O(carbonyl) interaction (Taylor & Kennard, 1982;Berkovitch-Yellin & Leiserowitz, 1984). Crystallization of N-(E-cinnamoyl)alanine (la) from glacial acetic acid yields crystals with the morphology shown in Fig.…”

Section: Polar Crystalsmentioning

confidence: 99%

Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using `tailor-made' auxiliaries

Weissbuch¹,

Popovitz‐Biro²,

Lahav³

et al. 1995

Acta Crystallogr B Struct Sci

331

288

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Tailor-made auxiliaries for the control of nucleation and growth of molecular crystals may be classified into two broad categories: inhibitors and promoters. Tailor-made inhibitors of crystal growth can be used for a variety of purposes, which include morphological engineering and etching, reduction of crystal symmetry, assignment of absolute structure of chiral molecules and polar crystals, elucidation of the effect of solvent on crystal growth, and crystallization of a desired polymorph. As for crystal growth promoters, monolayers of amphiphilic molecules on water have been used to induce the growth of a variety of three-dimensional crystals at the monolayer-solution interface by means of structural match, molecular complementarity or electrostatic interaction. A particular focus is made on the induced nucleation of ice by mono- © 1995 International Union of Crystallography Printed in Great Britain -all fights reserved layers of water-insoluble aliphatic alcohols. The twodimensional crystalline structures of such monolayers have been studied by grazing incidence X-ray diffraction. It has become possible to monitor, by this method, the growth, dissolution and structure of self-aggregated crystalline monolayers, and indeed multilayers, affected by the interaction of solvent molecules in the aqueous subphase with the amphiphilic headgroups, and by the use of tailor-made amphiphilic additives.

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“…6 In this study we test the ability of our method to predict correctly the crystal structure of acetic acid. 19 This structure is an interesting one, as it shows a catemer motif as opposed to almost all other carboxylic acids, which crystallize as cyclic dimers. Almost 20 years ago, Derissen and Smit 20 searched for possible dimer struc-Ž tures using fixed cell dimensions in space group .…”

Section: Introductionmentioning

confidence: 97%

Crystal structure predictions for acetic acid

et al. 1998

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Hydrogen bond studies. XLIV. Neutron diffraction study of acetic acid

Cited by 146 publications

References 7 publications

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a

Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using `tailor-made' auxiliaries

Crystal structure predictions for acetic acid

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Hydrogen bond studies. XLIV. Neutron diffraction study of acetic acid

Cited by 146 publications

References 7 publications

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe2compared with those of Ac‐l‐Ala‐NMe2, Ac‐dl‐Ala‐NMe2and other dimethylamidesa

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe2compared with those of Ac‐l‐Ala‐NMe2, Ac‐dl‐Ala‐NMe2and other dimethylamidesa

Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using `tailor-made' auxiliaries

Crystal structure predictions for acetic acid

Contact Info

Product

Resources

About

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a

Conformational investigation of α,β‐dehydropeptides. X. Molecular and crystal structure of Ac‐ΔAla‐NMe₂compared with those of Ac‐l‐Ala‐NMe₂, Ac‐dl‐Ala‐NMe₂and other dimethylamides^a