- Hydrogen-bonded cyclic dimers at large compression: The case of 1h-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole
-
1H-pyrrolo[3,2-h]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H···N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP).
- Chumak, Taisiia,Kurzyd?owski, Dominik,Listkowski, Arkadiusz,Rogo?a, Jakub
-
supporting information
(2021/07/10)
-
- Design and synthesis of chiral 1,10-phenanthroline ligand, and application in palladium catalyzed asymmetric 1,4-addition reactions
-
Pd-catalyzed asymmetric 1,4-addition of phenylboronic acid to α,β-unsaturated carbonyl compounds was developed using chiral 1,10-phenanthroline derivative as ligand. Good yields (up to 97%), and high enantioselectivities (up to 97% ee) were achieved.
- Tamura, Masafumi,Ogata, Hayato,Ishida, Yuu,Takahashi, Yasunori
-
p. 3808 - 3813
(2017/09/15)
-
- Selective ortho methylation of nitroheteroaryls by vicarious nucleophilic substitution
-
(Chemical Equation Presented) An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways under VNS conditions, one leading to an isoxazole and the other resulting in the formal cyclopropanation of an aromatic nitro compound.
- Achmatowicz, Michal,Thiel, Oliver R.,Gorins, Gilles,Goldstein, Corinne,Affouard, Caroline,Jensen, Randy,Larsen, Robert D.
-
p. 6793 - 6799
(2008/12/22)
-
- Synthesis and Some Properties of A New Class of Six Membered Heteroaromatic Betains, 3H-Pyridobenzotriazin-4-ylium-3-ides
-
A series of 3H-pyridobenzotriazin-4-ylium-3-ides has been synthesised by reaction of 8-acylaminoquinolines with O-mesitylenesulphonylhydroxylamine followed by treatment with aqueous alkali.The spectral (u.v., 1H n.m.r., and 13C n.m.r. spectra) and chemical properties (bromination and 1,3-dipolar cycloaddition) of the new mesomeric betains have been investigated.
- Ikeda, Masazumi,Yamagishi, Masafumi,Bayomi, Said M. M.,Miki, Yasuyoshi,Sumida, Yoshio,Tamura, Yasumitsu
-
p. 349 - 354
(2007/10/02)
-