1-Acetyl-2-thiohydantoin

Casas, José S.; Castiñeiras, A.; Couce, D.; Playá, Nuria; Sordo, José; Varela, José M.

doi:10.1107/s0108270197014960

Cited by 9 publications

(8 citation statements)

References 1 publication

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“…1(b) [C2-C3-C4-C5 52.2(2) °; N2-C3-C4-C5 -60.7(2) °]. Overall molecular geometries of 1-Ac-5-BTH are similar to those in 1-acetyl-2-thiohydantoin [21] . The acetyl group on the N2 atom is …”

Section: Crystal Structures Of 5-bth and 1-ac-5-bthmentioning

confidence: 54%

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Kunimoto

Ichitani

Ogawa

et al. 2009

Spectroscopy Letters

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Abstract:The crystal structures of 5-benzyl-2-thiohydantoin (5-BTH) and 1-acetyl-5-benzyl-2-thiohydantoin (1-Ac-5-BTH) have been determined by X-ray diffraction. In the 5-BTH crystals, the enantiomeric (R)-and (S)-5-BTH molecules are connected to form cyclic dimers via the hydrogen bonds of the thioamide and the amide moieties. On the other hand, the intermolecular hydrogen bonds in 1-Ac-5-BTH crystals form an infinite chain. These differences 1 SpectroscLett_kunimoto_revised in the hydrogen bond pattern are also discussed in the IR and Raman spectra. The ab initio molecular orbital calculations (Gaussian 03) with 6-31G(d,p) basis set were carried out for 5-BTH and 1-Ac-5-BTH to get the preferred conformation.

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Section: Crystal Structures Of 5-bth and 1-ac-5-bthmentioning

confidence: 54%

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Kunimoto

Ichitani

Ogawa

et al. 2009

Spectroscopy Letters

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“…The N1ÐC2ÐS2 angle is greater than the N3ÐC2ÐS2 angle (Table 1). This difference is also observed in the two N-acetylthiohydantoin compounds reported in the CSD [refcodes KOMGUO (Mackay et al, 1992), with angles of 130.6 and 123.4 , and NIFHIT (Casas et al, 1998), with angles of 132.0 and 121.9 ]. The average values for the same angle in the 36 fragments searched above are 127.7 and 125.2 , respectively.…”

mentioning

confidence: 67%

Hydrogen-bonding patterns inrac-1-acetyl-5-methyl-2-thioxoimidazolidin-4-one

et al. 2007

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“…Moreover, the compounds in the above categories possess potential anticarcinogenic, antimutagenic, antithyroidal, and antiviral activities . The calculated geometrical parameters such as bond lengths, bond angles and dihedral angles of these molecules using various density functionals were compared with the values obtained from their crystal structures . Initially 6–31 + G* basis set is used which is then extended to other higher basis sets.…”

Section: Resultsmentioning

confidence: 99%

“…Three known biologically important thione systems including simple derivatives of thiosemicarbazide, thiohydantoin and bornane‐2‐thione were chosen for the study. These systems were selected as their crystal structures were well characterized experimentally (Figure ) and have alpha hydrogen for thione–thiol tautomerization . The performance of DFT functionals in both geometry and energy calculations was evaluated.…”

Section: Methodsmentioning

confidence: 99%

Density functional evaluation and a feasibility study of intramolecular thione-thiol tautomerization

Jayasree

Sreedevi

2017

Int J Quantum Chem

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Performance of various density functionals for use in geometry and energetics calculation of thiocarbonyl systems is evaluated. The three biologically significant systems such as 2-methyl-3-thiosemicarbazide, 1-acetyl-2-thiohydantoin and bornane-2-thione are selected for the geometry analysis. Energy of tautomerization of thioacetone and enthalpy of formation of 2thiohydantoin are considered for analyzing the performance in energetics. Minnesota functionals such as M05-2X, M06-2X and range separated hybrid functional wB97 give best results in both geometry and energetics calculations. Studies on basis set effect showed reliable performance by 6-31 1 G* and 6-3111G** over higher basis sets. Feasibility of tautomerization in the aforementioned thiones has been investigated using the best performing density functionals.The proposed thione-thiol tautomerization step during PPC-DC catalyzed decarboxylation reaction has also been investigated and the computed high energy barrier shows less feasibility of the reaction. K E Y W O R D S basis set effect, calibration, density functionals, tautomerization, thiocarbonyl systems 1 | I N T R O D U C T I O NThiocarbonyl compounds are fascinating molecules with wide range of biological activities. [1][2][3] Tautomerization in thiocarbonyl systems, in particular, has been found to be one of the significant steps in certain enzymatic reactions and in many physiological processes. [4][5][6][7][8] The studies that detail the importance of thione moiety in antithyroid agents and the effect of thione-thiol tautomerism on peroxidasecatalysed oxidation reactions and 4 0 -phosphopantothenoylcysteine decarboxylase (PPC-DC) catalyzed decarboxylation reaction were reported. [7,8] There were reports that also show the tautomerization of thiobases such as thiouracil and thiocytosine which are the constituents of t-RNA species. [4] The significance of thione-thiol tautomerism in these physiological processes demands a detailed study of its energetics. [9,10] Density functional theory (DFT) has become a powerful and time effective method for the calculation of electronic structure and other molecular properties nowadays. [11][12][13][14][15][16] Wide application of DFT methods evinces its unparallel impact on quantum mechanics to solve challenging problems in chemistry. Various DFT methods differ in their exchange-correlation functionals and this difference makes the best functional for one application often not the best for the other. [17] Therefore, the selection of a density functional from a plethora of reported exchange correlation functionals for a particular chemical problem becomes essential. Several such calibration studies have been reported. [18][19][20][21][22][23][24][25][26] Methods such as BP86 and B3LYP were found to perform well for the analysis of intermediate and transition state structures and the relative energy calculations of chemical processes. [21] However, our initial studies using B3LYP/6-31 1 G* produced a contradictory result for the geometry of simple carbonyl sys...

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1-Acetyl-2-thiohydantoin

Cited by 9 publications

References 1 publication

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Hydrogen-bonding patterns inrac-1-acetyl-5-methyl-2-thioxoimidazolidin-4-one

Density functional evaluation and a feasibility study of intramolecular thione-thiol tautomerization

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