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Synthesis, crystal structure and dynamic behavior of naphthalene-based calix[3]amide: Cyclic trimers of 2-alkylamino-6-naphthoic acid

✍ Scribed by Kosuke Katagiri; Kanako Sawano; Miho Okada; Shiho Yoshiyasu; Reiko Shiroyama; Norio Ikejima; Hyuma Masu; Takako Kato; Masahide Tominaga; Isao Azumaya


Book ID
103838316
Publisher
Elsevier Science
Year
2008
Tongue
English
Weight
851 KB
Volume
891
Category
Article
ISSN
0022-2860

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✦ Synopsis


Treatment of 6-amino-2-naphthoic acid with dichlorotriphenylphosphorane afforded a new naphthalene ring-based calix[3]amide in moderate yield. The macrocyclic calix[3]amide exists in an anti-form in the crystalline state and forms a channel structure along its b axis. In CDCl3 solution it exists in equilibrium between the syn-and anti-forms in solution (100:57). The energy barrier between the anti-to syn-forms was calculated to be 17.8 ± 0.2 kcal/mol.