Hindered rotation in N-methylthiourea

Tompa, Albert S.; Barefoot, Rupert D.; Price, E.

doi:10.1021/j100722a029

Cited by 25 publications

(7 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Surprisingly, in the case of the thiourea derivative 9, the spectrum in deuteriodimethylsulfoxide (DMSO-d 6 ) showed the presence of two species at a ratio of 34-66%. This result was interpreted as indicating the existence under the experimental conditions of two configurations of the thiourea due to the restricted rotation around the C-N bond as reported by Tompa et al 9) From the dissymmetry of the thiourea, the (Z) and (E)-conformations could concern either the NH linked to the phenyl ring or the imidazo[1,2-a]pyridinic moiety. Using 1 H-1 H correlation spectroscopy (COSY) and X-H correlation spectroscopy (XHCOR) all the resonances could be assigned.…”

Section: Chemistrysupporting

confidence: 69%

3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents.

Chaouni-Benabdallah

Galtier

Allouchi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

This work reports the synthesis and the antiviral activities of 3-benzamido, 3-phenylureido and 3-phenylthioureido derivatives in the imidazo[1,2-a]pyridine series. The structure was proven by NMR spectroscopy. The synthesized compounds were evaluated against a large number of viruses. The 3-phenylthioureido derivative 7 showed moderate activity against human cytomegalovirus (HCMV) in vitro. The crystallographic data for 8 are also reported and explain the absence of activity against human immunodeficiency virus (HIV).

show abstract

Section: Chemistrysupporting

confidence: 69%

3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents.

Chaouni-Benabdallah

Galtier

Allouchi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…(20). Given this explanation the interpretation of the spectra of _N-inethyl thiourea (18) and N,d,Pdldimethyl thiourea (Fig. I) hllows naturally.…”

Section: Introductionmentioning

confidence: 85%

“…A recent study discusses restricted rotation in N-methyl thiourea using n.m.r. as the experimental technique (18). The structures of urea and thiourea constitute a classic problem involving tautomerism but there is now a concensus of opinion that 1 rather than 2 is correct (19).…”

Section: Introductionmentioning

confidence: 99%

Nuclear Magnetic Resonance Studies of Co(II) Complexes of Thiourea and Related Ligands

Eaton¹,

Zaw²

1971

Can. J. Chem.

View full text Add to dashboard Cite

A number of tetrahedral Co(I1) complexes of thiourea, N-methyl thiourea, and N,N'-dimethyl thiourea have been studied by nuclear magnetic resonance (n.m.r.). All the complexes are paramagnetic and the proton resonances show large isotropic shifts in acetone-d6 solutions. The origin of these shifts is discussed. Two sets of resonances are observed for each position and this is attributed to restricted rotation about the C-N bond. The barrier for this rotation is higher in the complexes than in the free ligands. For all complexes the exchange between free and coordinated ligand is fast at room temperature but slow below -80 "C. The complexes are dissociated to a greater or lesser extent in acetone solution and equilibrium constants and other thermodynamic data are reported for this dissociation. Entropy differences are more important than energy differences in determining the extent of dissociation. It has been demonstrated that both associative and dissociative mechanisms play a part in the ligand exchange process. The relative importance of the two mechanisms differs in the various complexes. IntroductionMost transition metal complexes are labile. We define labile complexes as those for which ligand exchange occurs in a time shorter than, or comparable to, the time taken to perform an analytical experiment on the ligand distribution in the system. If proton n.m.r. is the chosen analytical method, as it is in our case, the relevant period is of the order of several minutes which represents the time needed to prepare a solution containing complex and free ligand and to obtain its n.m.r. spectrum. By this criterion Co(II1) complexes and some other complexes with multidentate ligands are stable or non-labile. Most other complexes are labile, even those containing "good" bidentate ligands such as P-diketones U,2).

show abstract

“…The N-alkyl substituted thiourea, with the coplanar N 2 CS skeletal atoms can take two possible conformational forms, trans and cis, whereas three different conformations are possible for N,N¢-dialkyl substituted thioureas the cis-cis, trans-trans and cis-trans isomers. NMR studies have been made in an effort to determine the extent of rotation about the S=CN bond in thioureas [10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Novel (E,E)-vic-dioximes

Kurtoğlu

Dağdelen

Toroğlu

2006

Transition Met Chem

View full text Add to dashboard Cite

A novel vic-dioxime ligand containing the thiourea group, (4E,5E)-1,3-bis{4-[(4-methylphenylamino)methyl] phenyl}-2-thiooxaimidazoline-4,5-dione dioxime, (4) mmdH 2 has been prepared from N,N¢-bis{4-[(4-methylphenylamino)methyl]phenyl}thiourea, (3) mft and cyanogen di-N-oxide. Mononuclear [M(mmdH) 2 ], where M=Ni II , Co II and Cu II complexes of the (4) mmdH 2 bidentate ligand have been obtained with a 1:2 metal:ligand ratio, as do most the vic-dioximes. The complexes are formed by coordination of N, N atoms of the ligand. The vic-dioxime ligand and its some transition metal complexes have been characterized by elemental analyses, molar conductance data, magnetic susceptibility, i.r., 1 H-n.m.r and u.v.-vis. spectroscopy. Conductivity measurements have shown that mononuclear complexes are non-electrolytes. In addition, the ligands and metal complexes were screened for antibacterial and antifungal activities by agar well diffusion techniques using DMF as solvent.

show abstract

Hindered rotation in N-methylthiourea

Cited by 25 publications

References 8 publications

3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents.

3-Benzamido, Ureido and Thioureidoimidazo[1,2-a]pyridine Derivatives as Potential Antiviral Agents.

Nuclear Magnetic Resonance Studies of Co(II) Complexes of Thiourea and Related Ligands

Synthesis and Biological Activity of Novel (E,E)-vic-dioximes

Contact Info

Product

Resources

About