Glycine hydrogen fluoride: Remarkable hydrogen bonding in the dimeric glycine glycinium cation

Fleck, Michel; Ghazaryan, V.V.; Petrosyan, A.M.

doi:10.1016/j.molstruc.2010.09.010

Cited by 17 publications

(4 citation statements)

References 16 publications

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“…This could be interpreted as the formation of either a strong O-HÁ Á ÁF hydrogen bond between l-cysteinium and fluoride ions [assuming the structure to have simple cations and anions, i.e. (l-CysH)F] or of an O-HÁ Á ÁO hydrogen bond [if the structure consisted of (l-CysÁ Á Ál-CysH)(FÁ Á ÁH-F) entities, as in the case of glycinium hydrogen fluoride] (Fleck et al, 2010). The results of the structure solution confirmed neither of these two options, but 'an unprecedented structural motif' l-CysH(l-CysÁ Á Ál-CysH)F(FÁ Á ÁH-F) was instead revealed.…”

Section: Introductionmentioning

confidence: 99%

Unusual hydrogen bonding inL-cysteine hydrogen fluoride

Minkov

Ghazaryan

Болдырева

et al. 2015

Acta Crystallogr C Struct Chem

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L-Cysteine hydrogen fluoride, or bis(L-cysteinium) difluoride-L-cysteine-hydrogen fluoride (1/1/1), 2C3H8NO2S(+)·2F(-)·C3H7NO2S·HF or L-Cys(+)(L-Cys···L-Cys(+))F(-)(F(-)...H-F), provides the first example of a structure with cations of the 'triglycine sulfate' type, i.e. A(+)(A···A(+)) (where A and A(+) are the zwitterionic and cationic states of an amino acid, respectively), without a doubly charged counter-ion. The salt crystallizes in the monoclinic system with the space group P2(1). The dimeric (L-Cys···L-Cys(+)) cation and the dimeric (F(-)···H-F) anion are formed via strong O-H···O or F-H···F hydrogen bonds, respectively, with very short O···O [2.4438 (19) Å] and F···F distances [2.2676 (17) Å]. The F···F distance is significantly shorter than in solid hydrogen fluoride. Additionally, there is another very short hydrogen bond, of O-H···F type, formed by a L-cysteinium cation and a fluoride ion. The corresponding O···F distance of 2.3412 (19) Å seems to be the shortest among O-H···F and F-H···O hydrogen bonds known to date. The single-crystal X-ray diffraction study was complemented by IR spectroscopy. Of special interest was the spectral region of vibrations related to the above-mentioned hydrogen bonds.

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Section: Introductionmentioning

confidence: 99%

Unusual hydrogen bonding inL-cysteine hydrogen fluoride

Minkov

Ghazaryan

Болдырева

et al. 2015

Acta Crystallogr C Struct Chem

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“…[18][19][20] Glycine is also known to form both organic and inorganic salts with a variety of acids, many of which are considered to be promising optical, ferroelectric and piezoelectric materials. [21][22][23][24][25][26][27][28][29][30][31][32][33][34] The pharmaceutical industry also makes use of glycine both as an excipient and an active pharmaceutical ingredient, 35 therefore its salts and co-crystals can be of interest for pharmaceutical applications.…”

Section: Introductionmentioning

confidence: 99%

The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation. A comparison of different crystallisation techniques

Losev¹,

Михайленко²,

Achkasov³

et al. 2013

New J. Chem.

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“…Crystal and molecular structures of salts obtained in form of good quality single crystals have been determined by the single-crystal X-ray diffraction method. The details of structure determination and registration of the spectra are given in our previous publications [3][4][5][6][7][8][9][10].…”

Section: Methodsmentioning

confidence: 99%

“…Nevertheless-as we have devoted much research on crystalline salts of various amino acids over the last years-we were surprised that the salts of amino acids with hexafluorosilicate anion have not been investigated previously. The only relevant paper is [2], where the authors obtained the crystal of sodium tris(glycinium) bis(hexafluorosilicate) glycine trisolvate when they tried to obtain glycinium fluoride in glass containers (see also [3]). …”

Section: Introductionmentioning

confidence: 99%