The Crystal Structure of 2-(o-Hydroxyphenyl)benzothiazole.

Sténson, Per; Zeppezauer, E.; Boive, T.; Nordström, B.; Brändén, Carl‐Ivar

doi:10.3891/acta.chem.scand.24-3729

Cited by 49 publications

(29 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The crystallographic data are readily available for HBT [58] and 2-(3-methoxy-2-hydroxyphenyl)benzimidazole (MHBI) [59]. Table 1 compares the calculated parameters of the optimized ground state geometries with the crystallographic data for both the molecular systems [60].…”

Section: Resultsmentioning

confidence: 99%

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

Purkayastha

Chattopadhyay

2003

IJMS

View full text Add to dashboard Cite

Two series of compounds, one comprising of 2-(2′-hydroxyphenyl)benzoxazole (HBO), 2-(2′-hydroxyphenyl)benzimidazole (HBI), 2-(2′-hydroxyphenyl)benzothiazole (HBT), and the other of 2-(2′-hydroxyphenyl)oxazole (HPO), 2-(2′-hydroxyphenyl)imidazole (HPI) and 2-(2′-hydroxyphenyl)thiazole (HPT) are susceptible to ground state rotamerization as well as excited state intramolecular proton transfer (ESIPT) reactions. Some of these compounds show experimental evidence of the existence of two ground state conformers. Out of these two one undergoes ESIPT reaction leading to the formation of the tautomer. The two photophysical processes, in combination, result in the production of a number of fluorescence bands each one of which corresponding to a particular species. Semiempirical AM1-SCI calculations have been performed to rationalize the photophysical behaviour of the compounds. The calculations suggest that for the first series of compounds, two rotational isomers are present in the ground state of HBO and HBI while HBT has a single conformer under similar circumstances. For the molecules of the other series existence of rotamers depends very much on the polarity of the environment. The potential energy curves (PEC) for the ESIPT process in different electronic states of the molecules have been generated theoretically. The simulated PECs reveal that for all these systems the IPT reaction is unfavourable in the ground state but feasible, both kinetically and thermodynamically, in the S 1 as well as T 1 states.

show abstract

Section: Resultsmentioning

confidence: 99%

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

Purkayastha

Chattopadhyay

2003

IJMS

View full text Add to dashboard Cite

show abstract

“…The angle at the sulphur atom, 90.2 °, is common for substituted thiazole molecules. 1-763 1.297 2-Methylaminobenzothiazole (Fehlmann, 1970) 1.763 1.297 Phenylthiazolidinedione (Matthews, 1964) 1.776 1.338 2-(O-Hydroxy-phenyl) benzothiazole (Stenson, 1970) 1-749 1.280 N-Benzyl-4-methylthiazolium bromide (Power et al, 1970) 1"671 1.308 Sulphathiazole II (Kruger & Gafner, 1971) 1.742 1.332 2-Amino-4-thiazolidinone-5-acetic acid (Amirthalingham & Muralidharan, 1972a) 1.726 1.361 1.336 1"338 2-Imino-4-thiazolidinone (Amirthalingham & Muralidharan, 1972b) The exocyclic, C(2)-N(2), and heterocyclic, C(2)-N(3), bonds possess 60 and 40% double-bond character respectively, on Wheatley's (1955) scale. This is indicative of amino-imino tautomerism in the neutral molecule.…”

Section: D's In Parentheses C(2)--s(1) --C(5) 90"2 (7) ° H(1)--o(1)-mentioning

confidence: 99%

The crystal and molecular structure of 2-amino-4-phenylthiazole hydrobromide monohydrate

Form¹,

Raper²,

Downie³

1974

Acta Crystallogr Sect B

View full text Add to dashboard Cite

“…In the thiazole ring of benzothiazole, formed by the condensation of the aldehydic group in anisaldehyde with an amino and thiol of o-aminothiophenol, the C(7)-N(1) bond length of 1.318(2) Ǻ is shorter than the C(1)-S(1) and C(7)-S(1) of 1.7367(18) Ǻ and 1.7141(15) Ǻ in the aromatic system. The other bond lengths are intermediate between ideal values of corresponding single and double bonds giving evidence for extended π-delocalization throughout the entire molecule [42] (figure 2). The orientation of methoxy group is cis to S(1) of the thiazole ring.…”

Section: Resultsmentioning

confidence: 89%

Synthesis, spectral, and magnetic studies of benzothiazolium tetrachlorocuprate salts: crystal structure and semiconducting behavior of bis[2-(4-methoxyphenyl)benzothiazolium] tetrachlorocuprate(II)

Devi

Ravindran²,

Fazil³

et al. 2015

Journal of Coordination Chemistry

View full text Add to dashboard Cite

The Crystal Structure of 2-(o-Hydroxyphenyl)benzothiazole.

Cited by 49 publications

References 0 publications

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

The crystal and molecular structure of 2-amino-4-phenylthiazole hydrobromide monohydrate

Synthesis, spectral, and magnetic studies of benzothiazolium tetrachlorocuprate salts: crystal structure and semiconducting behavior of bis[2-(4-methoxyphenyl)benzothiazolium] tetrachlorocuprate(II)

Contact Info

Product

Resources

About