Looking at aniline-phenol recognition in molecular crystals: an evergreen endeavour

Sood, Ankush; Desiraju, Gautam R.

doi:10.1007/s11224-016-0869-8

Cited by 2 publications

(5 citation statements)

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“…These frequencies were almost the same as the 3525 cm –1 of O–H stretching in 1 (OH, OH) and 3478 and 3383 cm –1 of N–H stretching in 1 (NH 2 , NH 2 ). These results show that OH and NH 2 groups of 1 (OH, NH 2 ) do not interact each other even in the solid state …”

Section: Resultsmentioning

confidence: 77%

“…The chemical shifts remained unchanged from 0.5 mM to a saturated concentration of about 3.5 mM, independent of concentration. These observations indicate that the OH and NH 2 groups within the well-defined cavity of 1 (OH, NH 2 ) do not interact with each other either intra- or intermolecularly and prevent self-association in CDCl 3 . In the IR spectrum of the solid of 1 (OH, NH 2 ), the peaks corresponding to O–H stretching were observed at 3539 cm –1 and the peaks corresponding to N–H stretching was observed at 3473 and 3378 cm –1 (Figure S18).…”

Section: Resultsmentioning

confidence: 93%

“…These observations indicate that the OH and NH 2 groups within the well-defined cavity of 1 (OH, NH 2 ) do not interact with each other either intra- or intermolecularly and prevent self-association in CDCl 3 . 10 In the IR spectrum of the solid of 1 (OH, NH 2 ), the peaks corresponding to O–H stretching were observed at 3539 cm –1 and the peaks corresponding to N–H stretching was observed at 3473 and 3378 cm –1 ( Figure S18 ). These frequencies were almost the same as the 3525 cm –1 of O–H stretching in 1 (OH, OH) and 3478 and 3383 cm –1 of N–H stretching in 1 (NH 2 , NH 2 ).…”

Section: Resultsmentioning

confidence: 99%

“…This molecular design allows endo -functionalization of the macrocycle 1 by using appropriate m -phenylene units with the desired functional groups (Figure ). We expected that introduced different functional groups such as OH and NH 2 in the macrocycle 1 could work independently toward guest molecules because these functional groups at the distal positions could not show intramolecular interactions, although phenol and aniline are known to interact each other in both solution and the solid state …”

Section: Resultsmentioning

confidence: 99%

“…These results show that OH and NH 2 groups of 1 (OH, NH 2 ) do not interact each other even in the solid state. 10 …”

Section: Resultsmentioning

confidence: 99%

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Endo-Functionalized Cyclic Oligophenylenes: Synthesis and Complexation with a Chiral Phosphoric Acid

et al. 2022

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The synthesis of endo-functionalized cyclic oligophenylenes in which adjacent benzene rings are perpendicular to one another is described. Annulation precursors, OH-or NH 2functionalized quinquephenyl diboronic acids, and septiphenyl dibromo compounds were systematically prepared by using a diprotected biphenyl-3,4′-diyl diboronic acid as a key compound. Four endo-functionalized cyclic oligophenylenes were synthesized by annulation of the precursors in dilute conditions through Suzuki−Miyaura cross-coupling. X-ray analysis of the macrocycle revealed the unique 1D channel packing structure formed by connecting the nanometer-sized cavity of the macrocycle. Furthermore, NH 2 -functionalized macrocycles could bind a chiral phosphoric acid in the cavity in CDCl 3 solution.

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Section: Resultsmentioning

confidence: 77%

Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…These results show that OH and NH 2 groups of 1 (OH, NH 2 ) do not interact each other even in the solid state. 10 …”

Section: Resultsmentioning

confidence: 99%