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Molecules, Volume 2, Issue 7 (July 1997), Pages 100-113, Articles M23-M24

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Open AccessArticle Amberlyst 15 Catalyzed Prenylation of Phenols: One-Step Synthesis of Benzopyrans
Molecules 1997, 2(7), 100-105; doi:10.3390/20700100
Received: 23 May 1997 / Accepted: 4 June 1997 / Published: 30 July 1997
Cited by 23 | PDF Full-text (43 KB)
Abstract A convenient one-step synthesis of 2,2-dimethylchromans and chromenes using Amberlyst 15 as a catalyst is described. Full article
Open AccessArticle (R,R)-Tartaric Acid Dimethyl Diester from X-Ray and Ab Initio Studies: Factors Influencing Its Conformation and Packing
Molecules 1997, 2(7), 106-113; doi:10.3390/20700106
Received: 14 February 1997 / Accepted: 10 April 1997 / Published: 20 July 1997
Cited by 16 | PDF Full-text (143 KB)
Abstract
The conformation of dimethyl (R,R)-tartrate has been analyzed on the basis of the single crystal X-ray diffraction method as well as by ab-initio quantum chemical studies. The results showed that the extended T conformation containing two planar hydroxyester moieties predominates in both ab-initio
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The conformation of dimethyl (R,R)-tartrate has been analyzed on the basis of the single crystal X-ray diffraction method as well as by ab-initio quantum chemical studies. The results showed that the extended T conformation containing two planar hydroxyester moieties predominates in both ab-initio and X-ray studies. The lowest energy conformer in ab-initio calculations has C2 symmetry and hydrogen bonds between a hydroxyl group and the nearest carbonyl oxygen. The second in energetical sequence, with an energy difference of only 1.2 kcal/mol, is the asymmetrical conformer, which differs from the lowest energy form by the rotation of one of the ester groups by 180°. Intramolecular OH...O hydrogen bonds observed in this rotamer again involve only proximal functional groups. This conformer is present in the crystal structure of the studied compound, although its conformation in the solid state is no longer stabilized by intramolecular hydrogen bonds of the type mentioned above. In the crystal, hydroxyl groups are mostly involved in intermolecular hydrogen bonds and form only a weak intramolecular hydrogen bond with each other. The planar arrangement of the α-hydroxyester moieties combined with the extended conformation of the carbon chain seems to be stabilized by the intramolecular hydrogen bonds between neighboring functional groups and by the long range dipole-dipole interactions between two pairs of CO and (β)C-H bonds. Full article

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Open AccessShort Note Synthesis of 3-Bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-amide
Molecules 1997, 2(7), M23; doi:10.3390/M23
Received: 20 June 1997 / Published: 4 July 1997
PDF Full-text (89 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Open AccessShort Note Synthesis of 3-Bromo-2-ethoxy-4-methyl-3,4-dihydro-2H-pyran-6-amide
Molecules 1997, 2(7), M24; doi:10.3390/M24
Received: 20 June 1997 / Published: 4 July 1997
PDF Full-text (83 KB) | Supplementary Files
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

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