title: 2-Pyridone and 3-oxo-1,2,6-thiadiazine-1,1-dioxide derivatives: a new class of hydrogen bond equivalents of uracil.
abstract: Hydrogen bond complex stability between adenine (A) and hydrogen bond equivalents of uracil: 2-pyridone derivatives (U(X2O)X) and 3-oxo-1,2,6-thiadiazine-1,1-dioxide derivatives (U(SO2)X) was studied, and as the result, the hydrogen bond energy of U(X2O)X-A and a complex of UX(SO2)X-A, was about 1.5 kcal/mol more stable than that of the corresponding adenine-uracil derivatives complex, respectively. The energy difference between the imide tautomer and enol tautomer was smaller than those of uracil derivatives. U(SO2)F can form a stable complex with A, and its imide tautomer is stable.
authors.affiliation: National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki, 305-8565, Japan.
authors.forename: Shun-ichi
authors.initials: S
authors.lastname: Kawahara
authors.forename: Tadafumi
authors.initials: T
authors.lastname: Uchimaru
authors.forename: Kazunari
authors.initials: K
authors.lastname: Taira
mesh_terms: D000225:Adenine / Q000737:chemistry; D000465:Algorithms; D020029:Base Pairing; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D013816:Thermodynamics; D013829:Thiadiazines / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C487866:3-oxo-1,2,6-thiadiazine-1,1-dioxide; D011728:Pyridones; D013829:Thiadiazines; D014498:Uracil; C017679:2-hydroxypyridine; D000225:Adenine