Redox potential tuning in bio-relevant heterocycles via (anti)aromaticity modulated H-bonding (AMHB) was written by Kakeshpour, Tayeb;Van Wiemeersch, Adam;Jackson, James E.. And the article was included in Canadian Journal of Chemistry in 2020.Application In Synthesis of 1-Hydroxyisoquinoline This article mentions the following:
Hydrogen bonds are arguably the most important non-covalent interactions in chem. and biol., and their strength and directionality have been elegantly exploited in the rational design of complex structures. We recently noted that the variable responses of cyclic 蟺-systems upon H-bond formation reciprocally lead to modulations of the H-bonds鈥?strengths, a phenomenon that we dubbed (anti)aromaticity-modulated hydrogen bonding (AMHB) [J. Am. Chem. Soc.2016, 138, 3427-3432]. Species that switch from aromatic to antiarom. or vice versa upon changing 蟺-electron counts should be oppositely stabilized by the AMHB effects, so their redox potentials should be significantly “tuned” by H-bond formation. Herein, using quantum chem. simulations, we explore the effects of these H-bond induced 蟺-electron polarizations on the redox potentials of (anti)aromatic heterocycles. The systems chosen for this study have embedded amide groups and amidine moieties capable of forming two-point H-bonds in their cyclic 蟺-systems. Thus, as the 4-electron and 6-electron 蟺-systems in redox-capable monocycles (e.g., quinones) can be differentially stabilized, their redox potentials can be modulated by H-bond formation by as much as 6 kcal/mol (258 mV for one electron transfer). In fused rings, the connectivity patterns are as important as the 蟺-electron counts. Extending these ideas to flavin, a biol. relevant case, we find that H-bonding patterns like those found in its crystals can vary its redox potential by up to 1.3 kcal/mol. In the experiment, the researchers used many compounds, for example, 1-Hydroxyisoquinoline (cas: 491-30-5Application In Synthesis of 1-Hydroxyisoquinoline).
1-Hydroxyisoquinoline (cas: 491-30-5) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Application In Synthesis of 1-Hydroxyisoquinoline
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem