Gold-catalyzed domino cyclization to diverse polyheterocyclic frameworks: mechanism, origin of the cooperative hydrogen bond, and role of π-stacking interactions

2020 ◽  
Vol 10 (12) ◽  
pp. 4109-4118 ◽  
Author(s):  
Yunhe Li ◽  
Xiang Zhao
Keyword(s):  
Hydrogen Bond ◽  
Stacking Interactions ◽  
Detailed Mechanism ◽  
Cooperative Catalysis ◽  
Π Stacking ◽  
Cascade Catalysis

The detailed mechanism and origins of gold-catalyzed domino cyclization to diverse fused polyheterocyclic frameworks by cooperative catalysis and cascade catalysis were studied systematically.

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

2001 ◽  
Vol 58 (1) ◽  
pp. 94-108 ◽  
Author(s):  
Craig J. Kelly ◽  
Janet M. S. Skakle ◽  
James L. Wardell ◽  
Solange M. S. V. Wardell ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Space Group ◽  
Rotation Axes ◽  
Π Stacking ◽  
Structural Database ◽  
A Chain

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H4I-4′ (1), are linked by three-centre I...O2N interactions into chains and these chains are linked into a three-dimensional framework by C—H...O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO2-4′ (2), the chains generated by the I...O2N interactions are again linked into a three-dimensional framework by C—H...O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I...O=S interactions: these chains are linked into sheets by a C—H...O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π...π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline, 3-O2NC6H4NHSO2C6H4I-4′ (4), there are R^2_2(8) rings formed by hard N—H...O=S hydrogen bonds and R^2_2(24) rings formed by two-centre I...nitro interactions, which together generate a chain of fused rings: the combination of a C—H...O hydrogen bond and aromatic π...π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO2C6H4I-4′ (5), are linked by N—H...O=S and C—H...O(nitro) hydrogen bonds into a chain containing alternating R^2_2(8) and R^2_2(10) rings, but there are no I...O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H4I-4′ (6), and the combination of an I...O=S interaction and a hard N—H...O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C—H...O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

2021 ◽  
Vol 77 (8) ◽  
pp. 834-838
Author(s):  
Mohamed El Hafi ◽  
Sanae Lahmidi ◽  
Lhoussaine El Ghayati ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Energy Calculation ◽  
Boat Conformation ◽  
Stacking Interactions ◽  
Π Stacking

The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-2-ylidene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intramolecular N—HDiazp...ODhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the bc plane are formed by N—HDiazp...ODhydp hydrogen bonds and slipped π–π stacking interactions. The layers are connected by additional slipped π–π stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.8%), H...O/O...H (23.5%) and H...C/C...H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N—H...O hydrogen-bond energy is 57.5 kJ mol−1.

Crystal Structure of 4-(1-Hydroxypropyl)- isochroman-1,3-dione

2009 ◽  
Vol 64 (3) ◽  
pp. 328-330 ◽  
Author(s):  
Akoun Abou ◽  
Severin D. Goulizan Bi ◽  
Leopold Kaboré ◽  
Abdoulaye Djandé ◽  
Adama Saba ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Title Compound ◽  
Stacking Interactions ◽  
Triclinic Space Group ◽  
Space Group ◽  
Compound C ◽  
Π Stacking

The title compound (C12H10O4) crystallizes in the triclinic space group P1̄ with a = 7.367(3), b = 8.1188(3), c = 9.549(5) Å, α = 74.034(1)°, β = 84.374(2)°, γ = 64.581(3)°, Z = 2, and dcalc = 1.462 g cm−3. It exhibits a strong intramolecular O-H···O hydrogen bond and exists as the exocyclic enolic tautomer as it has been observed in solution. The structure is stabilized by C-H···π, C-O···π and π-π stacking interactions between benzene and pyran rings.

scholarly journals Isomers and polymorphs of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadienes

2006 ◽  
Vol 62 (4) ◽  
pp. 666-675 ◽  
Author(s):  
Christopher Glidewell ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Space Group ◽  
Stacking Interaction ◽  
Space Groups ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Polymorphic Forms

The structures of five of the possible six isomers of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E,E)-1,4-Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 (I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P21/n and P21/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic π...π stacking interactions and C—H...π(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C—H...O hydrogen bonds. The molecules of (E,E)-1,4-bis(3-nitrophenyl)-2,3-diaza-1,3-butadiene (III) lie across inversion centres in the space group P21/n, and a combination of a C—H...O hydrogen bond and a π...π stacking interaction links the molecules into sheets. A total of four independent C—H...O hydrogen bonds link the molecules of (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P21/n, are linked by just two independent C—H...O hydrogen bonds into a three-dimensional framework.

Supramolecular structures of N 4-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines

2003 ◽  
Vol 59 (2) ◽  
pp. 263-276 ◽  
Author(s):  
Manuel Melguizo ◽  
Antonio Quesada ◽  
John N. Low ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Electronic Structures ◽  
Supramolecular Structure ◽  
Supramolecular Structures ◽  
Stacking Interactions ◽  
Molecular Electronic ◽  
Π Stacking

The molecular and supramolecular structures of eight N 4-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines are discussed, along with one analogue containing no nitroso substituent. The nitroso derivatives all exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding between the molecules. The intermolecular interactions include hard hydrogen bonds of N—H...O and N—H...N types, together with O—H...O and O—H...N types in the monohydrate of 2-amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine, soft hydrogen bonds of C—H...O, C—H...π(arene) and N—H...π(arene) types and aromatic π...π stacking interactions. The predominant supramolecular structure types take the form of chains and sheets, but no two of the structures determined here exhibit the same combination of hydrogen-bond types.

scholarly journals N-[2-(2-Hydroxyethoxy)phenethyl]phthalimide

2012 ◽  
Vol 68 (6) ◽  
pp. o1636-o1636
Author(s):  
Er-Qun Yang ◽  
Jun-Tao Zhang ◽  
Xiao-Ping Cao ◽  
Jin-Zhong Gu
Keyword(s):  
Hydrogen Bond ◽  
Network Structure ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Dimensional Network ◽  
Benzene Rings

The title compound, C18H17NO4, was obtained accidentally through acid-catalysed aromatization of a phthalimide-substituted 2-(1-hydroxyethyl)cyclohex-2-enone. It exhibits an intramolecular O—H...Oc (c = carbonyl) hydrogen bond and forms a three-dimensional network structure via π–π stacking interactions between adjacent benzene rings (phthalimide-to-phenylene and phthalimide-to-phthalimide), with centroid–centroid distances of 3.8262 (6) and 3.6245 (5) Å.

scholarly journals Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones

2015 ◽  
Vol 71 (7) ◽  
pp. 766-771
Author(s):  
Ligia R. Gomes ◽  
John Nicolson Low ◽  
Fernando Cagide ◽  
Fernanda Borges
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Mechanism Of Formation ◽  
Π Stacking ◽  
Heterocyclic Moiety

The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C13H8N2O3S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C14H10N2O3S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripyrrolidinylphosphonium hexafluoridophosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thiazolopyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intramolecular O—H...O hydrogen bond, which generates anS(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the molecules are linked by weak C—H...O hydrogen bonds and π–π stacking interactions.

Asymmetric Synthesis of Indolines through Intramolecular Shifting of Aromatic Sulfinyl Groups. Role of the π,π-Stacking Interactions in these Unusual SNAr Processes

2009 ◽  
Vol 131 (26) ◽  
pp. 9432-9441 ◽  
Author(s):  
José L. García Ruano ◽  
Alejandro Parra ◽  
Vanesa Marcos ◽  
Carlos del Pozo ◽  
Silvia Catalán ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Stacking Interactions ◽  
Π Stacking

Methyl (3aRS,3cRS,6cSR,7RS,8RS,8aSR)-2,5-bis(4-chlorophenyl)-7,9-bis(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3′,4′-f]pyrrolizine-3b-carboxylate dimethylformamide disolvate: a three-dimensional hydrogen-bonded framework

2012 ◽  
Vol 68 (11) ◽  
pp. o439-o442 ◽  
Author(s):  
Jairo Quiroga ◽  
Jaime Gálvez ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Mirror Symmetry ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Envelope Conformation ◽  
Π Stacking ◽  
Conformation Intermediate ◽  
Solvent Molecules ◽  
Molecular Components

The racemic title dipyrrolopyrrolizine compound crystallizes from dimethylformamide as a disolvate, C55H39Cl2N7O6·2C3H7NO. None of the four fused heterocyclic rings is planar; one adopts an envelope conformation, two others adopt half-chair conformations and the fourth adopts a conformation intermediate between an envelope and a half-chair. The arrangement of the ring fusions is such as to preclude the possibility of internal mirror symmetry. The three independent molecular components are weakly linked by C—H...O hydrogen bonds, and the dipyrrolopyrrolizine molecules are linked by a combination of four C—H...O and one C—H...π(arene) hydrogen bond to form a three-dimensional framework, from which the dimethylformamide solvent molecules are pendent. However, aromatic π–π stacking interactions are absent in the structure.

The Role of π−π Stacking Interactions in Square Planar Palladium Complexes. Combined Quantum Mechanics/Molecular Mechanics QM/MM Studies

2001 ◽  
Vol 20 (20) ◽  
pp. 4178-4184 ◽  
Author(s):  
Alessandra Magistrato ◽  
Paul S. Pregosin ◽  
Alberto Albinati ◽  
Ursula Rothlisberger
Keyword(s):  
Quantum Mechanics ◽  
Molecular Mechanics ◽  
Palladium Complexes ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Square Planar
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