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Volumn 4, Issue 4, 1992, Pages 222-226

Spontaneous racemization of chlorthalidone: kinetics and activation parameters

a Bolar Pharmaceutical Co Inc ^* (United States)

Author keywords

3 hydroxy 3 phenylphthalimidines; barrier to inversion; carbonium ion (intermediate in racemization); enantiomer interconversion; inversion (of configuration); rate constants (of inversion)

Indexed keywords

ANION; CHLORTALIDONE;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CONCENTRATION; ENANTIOMER; ENTROPY; EQUILIBRIUM CONSTANT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; RACEMIC MIXTURE; REACTION TIME; THERMODYNAMICS;

EID: 0026651877 PISSN: 08990042 EISSN: 1520636X Source Type: Journal
DOI: 10.1002/chir.530040404 Document Type: Article

Times cited : (21)

References (11)

1
- 84982507114
- Zur konstitution von benzophenone‐2‐carbonsäure‐derivaten
- (1959) Helvetica Chimica Acta , vol.42 , pp. 1085-1101
- Graf, W.¹ Girod, E.² Schmid, E.³ Stoll, W.G.⁴

2
- 0018854307
- Chromatographic resolutions of racemates. IX. Chlorotalidone, chlorotalidone methyl ether, and oxazepam enantiomers
- (1980) Chem. Ber. , vol.113 , pp. 2031-2035
- Blaschke, G.¹ Markgraf, H.²

3
- 84989467620
- Under acidic conditions the reaction proceeds in the sequence: 1 → 4 → 3; alkyl substitution at nitrogen renders imine 4b most stable to further hydrolysis. In strongly alkaline solution direct deamination occurs: 1 → 3; this reaction may involve lactam cleavage to a transient α‐hydroxy amine intermediate with subsequent base‐catalyzed E2 elimination to form the phenone (3).

4
- 0001774709
- Carbonium ions in solution. 9. The relationship between carbocations in superacid and solvolysis transition states
- N2 reactions
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 522-526
- Arnett, E.M.¹ Petro, C.² Schleyer³

5
- 84989467619
- The unusual capability of the CTD carbonium ion for resonance stabilization was first noted by Graf et al. (see ref. 1); delocalization of the positive charge to nitrogen through an equivalent carbonium‐immonium ion facilitates proton elimination.

6
- 84989473586
- eq at pH 12.0, these values agreed within one standard deviation (CV = 4%) with the data in Table 1.

7
- 84989495398
- 2c = 1.23 ± 0.05.

8
- 84989464932
- As seen in Figure 2, the arbitrary “endpoint” at which time the apex of the decreasing (−)‐1c peak was equidistant between the apex of the (+)‐1c peak and the valley separating the two apices, was determined by cut and weigh technique to represent the on‐column injection of a 51:49 enantiomeric ratio.

9
- 0004039791
- New York, Wiley‐Interscience
- (1972) Kinetic Stystems: Mathematical Description of Chemical Kinetics in Solution
- Capellos, C.¹ Bielski, B.H.J.²

10
- 0003466969
- Englewood Cliffs, NJ, Prentice‐Hall
- (1962) Physical Chemistry
- Moore, W.J.¹

11
- 0003617193
- New York, McGraw‐Hill
- (1941) The Theory of Rate Processes
- Glasstone, S.¹ Laidler, J.J.² Eyring, H.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.