The crystal and molecular structure of γ-aminobutyric acid determined at low temperature

Steward, E. G.; Player, R. B.; Warner, D.

doi:10.1107/s0567740873006072

Cited by 51 publications

(34 citation statements)

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“…The X-ray crystal structure of GABA was first determined by Steward, Player & Warner (1973). They found the molecule to be a zwitterion with a folded conformation ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Charge density in the crystal structure of γ-aminobutyric acid at 122 K – an intramolecular methylene H bridge

Craven¹,

Weber²

1983

Acta Crystallogr Sect B

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The charge density in y-aminobutyric acid (GABA) at 122 K has been determined from X-ray (Mo Ka) intensity data (3394 reflections with F o > 4a and sin 0/2 < 1.3 A-~). Least-squares refinements were carried out using Stewart's rigid pseudoatom model. Fixed neutron values were used for positional parameters and H-atom U u parameters. The sum of net atomic charges is -0.6 e for the carboxylate group and +0.6 e for the ammonium H atoms. The calculated molecular dipole moment is 13 (1) debye (1 debye = 3.336 x 10 -3° C m). Unexpectedly, there is a methylene H atom carrying a positive charge of +0.11 (2) e which forms an intramolecular bridge between negatively charged N and O atoms, -0.23 (3) and -0.15 (2)

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“…The X-ray crystal structure of GABA was first determined by Steward, Player & Warner (1973). They found the molecule to be a zwitterion with a folded conformation ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Charge density in the crystal structure of γ-aminobutyric acid at 122 K – an intramolecular methylene H bridge

Craven¹,

Weber²

1983

Acta Crystallogr Sect B

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“…Its formula is H 2 N-(CH 2 ) 3 -COOH. However, in solution and in the solid state, the chemical species can be in the form of zwitterions ϩ H 3 N-(CH 2 ) 3 -COO Ϫ while in the gas phase only the neutral form exists. This molecule has particular physico-chemical properties, due to the presence of the proton donor carboxyl acid (-COO) group and the proton acceptor amino (-NH 2 ).…”

mentioning

confidence: 99%

“…This molecule has particular physico-chemical properties, due to the presence of the proton donor carboxyl acid (-COO) group and the proton acceptor amino (-NH 2 ). GABA exists in two polymorphic forms: either the monoclinic structure with the space group (P2 1 /a) [3][4][5][6] or the tetragonal structure with the space group (I4 1 cd ). 7) The network of the intermolecular hydrogen bonds plays an essential role in the zwitterionic organisation of these crystal structures.…”

mentioning

confidence: 99%

“…7) The network of the intermolecular hydrogen bonds plays an essential role in the zwitterionic organisation of these crystal structures. The monoclinic and tetragonal crystals can be obtained respectively by crystallization in ethanol 3,4) or aqueous solution. 7) GABA is a major inhibitory neurotransmitter in the central nervous system and its biological characteristics were investigated in a previous paper.…”

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confidence: 99%

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Physico-Chemical Characterization of .GAMMA.-Amino n-Butyric Acid Nanoparticles

Dichi

Sghaier

Fraisse

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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This work deals with the preparation and characterization of high-purity nanoparticles of g g-amino n-butyric acid (GABA) in order to enhance the efficiency of this drug. A sublimation procedure at low pressure was applied to GABA after improving the experimental parameters of this physical transformation. The elaboration of the molecule is solvent-free. The process does not change the chemical formula of the compound but modifies its physico-chemical characteristics. In this work, we present the experimental parameters for preparing monoclinic GABA nanoparticles. Their identification and physico-chemical properties were determined with a large number of investigations: Powder X-ray diffraction (PXRD), density and purity measurements, differential scanning calorimetry (DSC), thermo-gravimetric analysis (TGA), calorimetric measurements (D DH dissolution and C p ), thermally stimulated current (TSC), and electrochemical impedance.

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“…Celle-ci parait &re li6e fi l'activit+ biochimique mise en +vidence pour les acides, DPA, et quelques homologues dont le plus actif est l'acide propyl-2 pent+ne-2 oique, C2Hs--CH=C(-C3HT)--COOH (PPA): ces acides sont des inhibiteurs comp6titifs de la GABA-transaminase (GABA-T), vis fi vis de son substrat, l'acide amino-4 butyrique, NH2-(CH2)3-COOH (GABA) (Simler, Ciesielski, Maitre, Randrianarisoa & Mandel, 1973;Ferrandes, Cohen-Addad, Benoit-Guyod & Eymard, 1974;Maitre, Ciesielski, Mandel, Taillandier, Benoit-Guyod & Boucherle, 1976). Cette activit~ peut &re reli~e fi l'analogie structurale entre la conformation cristalline des d6riv6s solides du DPA (le DPA est un liquide), du TPA et de ses d6riv6s et celle du GABA, pr+sentant, l'&at solide, une cha3ne repli6e (Tomita, Higashi & Fujiwara, 1973;Stewart, Player & Warner, 1973;Ferrandes et al, 1974;Cohen-Addad & Grand, 1974;Cohen-Addad & D'Assenza, 1976;Cohen-Addad, D'Assenza, TaiUandier & Benoit-Guyod, 1975. La conformation cristalline du PPA, bri~vement d~crite darts un autre article (Ciesielski, Cohen-Addad, Taillandier, Lajz~rowicz, Benoit-Guyod, Mandel & Boucherle, 1977), pr~sente, pour une partie de la mol6cule, une parfaite analogie avec la conformation repli~e du GABA.…”

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Structures cristallines de dérivés des acides dipropylacétique. VI. Composés homologues: comparaison de la propyl-3 hexène-3 amide et de l'acide propyl-2 penténe-2 öique

Cohen‐Addad¹,

Taillandier²

1977

Acta Crystallogr Sect B

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The crystal and molecular structure of γ-aminobutyric acid determined at low temperature

Cited by 51 publications

References 1 publication

Charge density in the crystal structure of γ-aminobutyric acid at 122 K – an intramolecular methylene H bridge

Charge density in the crystal structure of γ-aminobutyric acid at 122 K – an intramolecular methylene H bridge

Physico-Chemical Characterization of .GAMMA.-Amino n-Butyric Acid Nanoparticles

Structures cristallines de dérivés des acides dipropylacétique. VI. Composés homologues: comparaison de la propyl-3 hexène-3 amide et de l'acide propyl-2 penténe-2 öique

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