The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

Saeed, Aamer; Flörke, Ülrich; Erben, Mauricio F.

doi:10.1016/j.molstruc.2014.03.002

Cited by 26 publications

(13 citation statements)

References 68 publications

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“…Thirteen compounds were synthesized and their structures were confirmed by a combination of elemental analysis, infrared and nuclear magnetic resonance spectroscopy. 1-(Adamantane-1-carbonyl)-3-substituted thiourea compounds were prepared by the addition reaction between adamantyl isothiocyanate with a variety of suitably substituted anilines [ 22 , 23 , 24 , 25 ]. The starting material 1-adamantane carbonyl chloride was obtained via the reaction of 1-adamantane carboxylic acid with thionyl chloride.…”

Section: Methodsmentioning

confidence: 99%

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

et al. 2018

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Chronic pulmonary infection is a hallmark of lung disease in cystic fibrosis (CF). Infections dominated by non-fermentative Gram-negative bacilli are particularly difficult to treat and highlight an urgent need for the development of new class of agents to combat these infections. In this work, a small library comprising thiourea and guanidine derivatives with low molecular weight was designed; these derivatives were studied as antimicrobial agents against Gram-positive, Gram-negative, and a panel of drug-resistant clinical isolates recovered from patients with CF. One novel compound, a guanidine derivative bearing adamantane-1-carbonyl and 2-bromo-4,6-difluouro-phenyl substituents (H-BDF), showed potent bactericidal activity against the strains tested, at levels generally higher than those exhibited by tobramycin, ceftazimide and meropenem. The role that different substituents exert in the antimicrobial activity has been determined, highlighting the importance of the halo-phenyl group in the guanidine moiety. The new compound displays low levels of cytotoxicity against THP-1 and A549 cells with a selective index (SI) > 8 (patent application PCT/IB2017/054870, August 2017). Taken together, our results indicate that H-BDF can be considered as a promising antimicrobial agent.

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Section: Methodsmentioning

confidence: 99%

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

et al. 2018

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“…The lowest RMSD value for bond angles was obtained at B3LYP/6-311++G(d,p) level (see Table 1) indicating that this method reproduce better the experimental structure for the title compound. 3,3-disubstitued thiourea derivatives assume a twisted conformation in the solid state, with the sulfur and oxygen atoms pointing approximately in same directions [7,20,[40][41][42]. The structure of the 1-acylthioureas 3-monosubstituted and 3,3disubstituted generally show a significant influence of intramolecular hydrogen bonding, which results in substantial differences between the preferred conformation observed for these compounds [12].…”

Section: Computational Detailsmentioning

confidence: 99%

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

et al. 2015

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1-benzyl-3-furoyl-1-phenylthiourea is a thiourea derivative synthesized and characterized by means of vibrational spectroscopy (IR and Raman) multinuclear NMR ( 1 H and 13 C) and elemental analysis. The geometrical parameters of this compound obtained from XRD studies were compared with the calculated values [B3LYP/6-311++G(d,p)] showing a good agreement. As determined by XRD analysis performed previously, the title compound exhibits the U-shape conformation with the C=O and C=S double bonds in anticlinal geometry. This conformational feature is mainly dictated by the substitution degree on the thiourea core and the ability of forming and intramolecular N-H···O=C hydrogen bond. The UV-visible absorption spectra of the compound in methanol solution were recorded and analyzed using time dependent density functional theory (TD-DFT). Molecular stability was investigated by applying the natural bond (NBO) analysis. Intermolecular interactions were evaluated by means of AIM approach. The calculated HOMO and LUMO energies show that the charge transfer occurs in the molecule. The molecular electrostatic potential map was calculated by DFT method. Non-linear optical (NLO) behavior of the title compound was investigated by determining of electric dipole moment, polarizability α, and hyperpolarizability β using B3LYP/6-311++G(d,p) approximation.

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“…A recent review discusses various hydrogen bonding patterns of (substituted) thioureas42 and the role of substituents in the structures of thioureas are also described 43. The results exhibit the possibility for selectively addressing different hydrogen bonding motifs through unsymmetrical substitution patterns at the nitrogen donor atom.…”

Section: Resultsmentioning

confidence: 99%

Addressing Hydrogen Bonding Motifs by Suited Substitution of Thioureas

Hollmann

Oppermann

Amen

et al. 2016

Zeitschrift anorg allge chemie

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The possibility to form hydrogen bonds with different motifs is an interesting aspect of the chemistry of thioureas especially regarding catalysis. We present nine new thioureas with different unsymmetric substitution patterns involving aromatic and aliphatic substituents including the structural characterization of four of them. Herein, three different hydrogen bond patterns could be realized. Moreover, DFT calculations were performed to investigate the strength of the hydrogen * Prof. Dr. S. Herres-Pawlis E-Mail: sonja.herres-pawlis@ac.rwth-aachen.de [a] 660 bonds. Hereby, we show that we can selectively address different hydrogen bonding motifs by the choice of substituents. This enables a correlation of the molecular structure and the bonding motifs. Additionally, by natural resonance theory, we show that the contribution of the thiolate resonance form dominates the electronic structure, which is important for coordination chemistry.

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The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

Cited by 26 publications

References 68 publications

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

Addressing Hydrogen Bonding Motifs by Suited Substitution of Thioureas

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