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Search for "π-stacking" in Full Text gives 182 result(s) in Beilstein Journal of Organic Chemistry.
Symmetrical and unsymmetrical α,ω-nucleobase amide-conjugated systems
- Sławomir Boncel,
- Maciej Mączka,
- Krzysztof K. K. Koziol,
- Radosław Motyka and
- Krzysztof Z. Walczak
Beilstein J. Org. Chem. 2010, 6, No. 34, doi:10.3762/bjoc.6.34
- is shown in Figure 5. A proposal of simplified models of micro- and nanofibres is based on the π-stacking and hydrogen bonding interactions between thymine units. Amide bonds, on the other hand, may be crucial in the inter-layer hydrogen bonding. A linear system of hydrogen bonding appears as a
- ) less favourable “bent” system of hydrogen bonds; (C) π-stacking and hydrogen bonding based nanofibre; (D) longitudinal cross-section of a particular nanofibre. Synthesis of main acidic subunits, precursors of both symmetrical and unsymmetrical α,ω-nucleobase amide-conjugated systems: A – 5-substituted
Graphical Abstract
Figure 1: Examples of symmetrical and unsymmetrical α,ω-nucleobase amide-conjugated systems.
Scheme 1: Synthesis of main acidic subunits, precursors of both symmetrical and unsymmetrical α,ω-nucleobase ...
Figure 2: X-ray structure of 1ea shown as thermal ellipsoids at 50% probability [17,18].
Figure 3: DMT-MM in its presumably more stable conformation [20].
Figure 4: TEM images of symmetrical α,ω-nucleobase amide-conjugated systems: A – two splitting nucleoside nan...
Figure 5: Models of micro- and nanofibres based on hydrogen bonding interactions between thymine units; (A) t...
Molecular recognition of organic ammonium ions in solution using synthetic receptors
- Andreas Späth and
- Burkhard König
Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32
- ring. However, π–stacking interactions between the aromatic moiety and aromatic part of the amino acid contributes to the overall binding strength of the receptor. In transport experiments, chiral lariat ethers (Figure 18) show an increased flux of amino acids or their carboxylate salts and
- enantiomeric discrimination (Table 4): With preference for the R-enantiomers, the benzo- and naphtho-18-crown-6 33a and 33b generally revealed a larger flux of the aromatic amino acids or their salts than hosts 32a and 32b [164]. This was attributed to a strong π–π stacking interaction. The highest flux values
Graphical Abstract
Figure 1: Biologically important amines and quaternary ammonium salts: histamine (1), dopamine (2) and acetyl...
Figure 2: Crown ether 18-crown-6.
Figure 3: Conformations of 18-crown-6 (4) in solvents of different polarity.
Figure 4: Binding topologies of the ammonium ion depending on the crown ring size.
Figure 5: A “pseudorotaxane” structure consisting of 24-crown-8 and a secondary ammonium ion (5); R = Ph.
Figure 6: Typical examples of azacrown ethers, cryptands and related aza macrocycles.
Figure 7: Binding of ammonium to azacrown ethers and cryptands [111-113].
Figure 8: A 19-crown-6-ether with decalino blocking groups (11) and a thiazole-dibenzo-18-crown-6-ether (12).
Figure 9: 1,3-Bis(6-oxopyridazin-1-yl)propane derivatives 13 and 14 by Campayo et al.
Figure 10: Fluorescent azacrown-PET-sensors based on coumarin.
Figure 11: Two different pyridino-cryptands (17 and 18) compared to a pyridino-crown (19); chiral ammonium ion...
Figure 12: Pyridino-18-crown-6 ligand (21), a similar acridino-18-crown-6 ligand (22) and a structurally relat...
Figure 13: Ciral pyridine-azacrown ether receptors 24.
Figure 14: Chiral 15-crown-5 receptors 26 and an analogue 18-crown-6 ligand 27 derived from amino alcohols.
Figure 15: C2-symmetric chiral 18-crown-6 amino alcohol derivatives 28 and related macrocycles.
Figure 16: Macrocycles with diamide-diester groups (30).
Figure 17: C2-symmetric chiral aza-18-crown-6 ethers (31) with phenethylamine residues.
Figure 18: Chiral C-pivot p-methoxy-phenoxy-lariat ethers.
Figure 19: Chiral lariat crown ether 34.
Figure 20: Sucrose-based chiral crown ether receptors 36.
Figure 21: Permethylated fructooligosaccharide 37 showing induced-fit chiral recognition.
Figure 22: Biphenanthryl-18-crown-6 derivative 38.
Figure 23: Chiral lariat crown ethers derived from binol by Fuji et al.
Figure 24: Chiral phenolic crown ether 41 with “aryl chiral barriers” and guest amines.
Figure 25: Chiral bis-crown receptor 43 with a meso-ternaphthalene backbone.
Figure 26: Chromogenic pH-dependent bis-crown chemosensor 44 for diamines.
Figure 27: Triamine guests for binding to receptor 44.
Figure 28: Chiral bis-crown phenolphthalein chemosensors 46.
Figure 29: Crown ether amino acid 47.
Figure 30: Luminescent receptor 48 for bis-alkylammonium guests.
Figure 31: Luminescent CEAA (49a), a bis-CEAA receptor for amino acids (49b) and the structure of lysine bindi...
Figure 32: Luminescent CEAA tripeptide for binding small peptides.
Figure 33: Bis crown ether 51a self assembles co-operatively with C60-ammonium ion 51b.
Figure 34: Triptycene-based macrotricyclic dibenzo-[24]-crown-8 ether host 52 and guests.
Figure 35: Copper imido diacetic acid azacrown receptor 53a and the suggested His-Lys binding motif; a copper ...
Figure 36: Urea (54) and thiourea (55) benzo crown receptor for transport and extraction of amino acids.
Figure 37: Crown pyryliums ion receptors 56 for amino acids.
Figure 38: Ditopic sulfonamide bridged crown ether receptor 57.
Figure 39: Luminescent peptide receptor 58.
Figure 40: Luminescent receptor 59 for the detection of D-glucosamine hydrochloride in water/ethanol and lumin...
Figure 41: Guanidinium azacrown receptor 61 for simple amino acids and ditopic receptor 62 with crown ether an...
Figure 42: Chiral bicyclic guanidinium azacrown receptor 63 and similar receptor 64 for the enantioselective t...
Figure 43: Receptors for zwitterionic species based on luminescent CEAAs.
Figure 44: 1,10-Azacrown ethers with sugar podand arms and the anticancer agent busulfan.
Figure 45: Benzo-18-crown-6 modified β-cyclodextrin 69 and β-cyclodextrin functionalized with diaza-18-crown-6...
Figure 46: Receptors for colorimetric detection of primary and secondary ammonium ions.
Figure 47: Porphyrine-crown-receptors 72.
Figure 48: Porphyrin-crown ether conjugate 73 and fullerene-ammonium ion guest 74.
Figure 49: Calix[4]arene (75a), homooxocalix[4]arene (75b) and resorcin[4]arene (75c) compared (R = H, alkyl c...
Figure 50: Calix[4]arene and ammonium ion guest (R = H, alkyl, OAcyl etc.), possible binding sites; A: co-ordi...
Figure 51: Typical guests for studies with calixarenes and related molecules.
Figure 52: Lower rim modified p-tert-butylcalix[5]arenes 82.
Figure 53: The first example of a water soluble calixarene.
Figure 54: Sulfonated water soluble calix[n]arenes that bind ammonium ions.
Figure 55: Displacement assay for acetylcholine (3) with a sulfonato-calix[6]arene (84b).
Figure 56: Amino acid inclusion in p-sulfonatocalix[4]arene (84a).
Figure 57: Calixarene receptor family 86 with upper and lower rim functionalization.
Figure 58: Calix[6]arenes 87 with one carboxylic acid functionality.
Figure 59: Sulfonated calix[n]arenes with mono-substitution at the lower rim systematically studied on their r...
Figure 60: Cyclotetrachromotropylene host (91) and its binding to lysine (81c).
Figure 61: Calixarenes 92 and 93 with phosphonic acids groups.
Figure 62: Calix[4]arene tetraphosphonic acid (94a) and a double bridged analogue (94b).
Figure 63: Calix[4]arene tetraphosphonic acid ester (92c) for surface recognition experiments.
Figure 64: Calixarene receptors 95 with α-aminophosphonate groups.
Figure 65: A bridged homocalix[3]arene 95 and a distally bridged homocalix[4]crown 96.
Figure 66: Homocalix[3]arene ammonium ion receptor 97a and the Reichardt’s dye (97b) for colorimetric assays.
Figure 67: Chromogenic diazo-bridged calix[4]arene 98.
Figure 68: Calixarene receptor 99 by Huang et al.
Figure 69: Calixarenes 100 reported by Parisi et al.
Figure 70: Guest molecules for inclusion in calixarenes 100: DAP × 2 HCl (101a), APA (101b) and Lys-OMe × 2 HC...
Figure 71: Different N-linked peptido-calixarenes open and with glycol chain bridges.
Figure 72: (S)-1,1′-Bi-2-naphthol calixarene derivative 104 published by Kubo et al.
Figure 73: A chiral ammonium-ion receptor 105 based on the calix[4]arene skeleton.
Figure 74: R-/S-phenylalaninol functionalized calix[6]arenes 106a and 106b.
Figure 75: Capped homocalix[3]arene ammonium ion receptor 107.
Figure 76: Two C3 symmetric capped calix[6]arenes 108 and 109.
Figure 77: Phosphorous-containing rigidified calix[6]arene 110.
Figure 78: Calix[6]azacryptand 111.
Figure 79: Further substituted calix[6]azacryptands 112.
Figure 80: Resorcin[4]arene (75c) and the cavitands (113).
Figure 81: Tetrasulfonatomethylcalix[4]resorcinarene (114).
Figure 82: Resorcin[4]arenes (115a/b) and pyrogallo[4]arenes (115c, 116).
Figure 83: Displacement assay for acetylcholine (3) with tetracyanoresorcin[4]arene (117).
Figure 84: Tetramethoxy resorcinarene mono-crown-5 (118).
Figure 85: Components of a resorcinarene based displacement assay for ammonium ions.
Figure 86: Chiral basket resorcin[4]arenas 121.
Figure 87: Resorcinarenes with deeper cavitand structure (122).
Figure 88: Resorcinarene with partially open deeper cavitand structure (123).
Figure 89: Water-stabilized deep cavitands with partially structure (124, 125).
Figure 90: Charged cavitands 126 for tetralkylammonium ions.
Figure 91: Ditopic calix[4]arene receptor 127 capped with glycol chains.
Figure 92: A calix[5]arene dimer for diammonium salt recognition.
Figure 93: Calixarene parts 92c and 129 for the formation molecular capsules.
Figure 94: Encapsulation of a quaternary ammonium cation by two resorcin[4]arene molecules (NMe4+@[75c]2 × Cl−...
Figure 95: Encapsulation of a quaternary ammonium cation by six resorcin[4]arene molecules (NMe3D+@[130]6 × Cl−...
Figure 96: Structure and schematic of cucurbit[6]uril (CB[6], 131a).
Figure 97: Cyclohexanocucurbit[6]uril (CB′[6], 132) and the guest molecule spermine (133).
Figure 98: α,α,δ,δ-Tetramethylcucurbit[6]uril (134).
Figure 99: Structure of the cucurbituril-phthalhydrazide analogue 135.
Figure 100: Organic cavities for the displacement assay for amine differentiation.
Figure 101: Displacement assay methodology for diammonium- and related guests involving cucurbiturils and some ...
Figure 102: Nor-seco-Cucurbituril (±)-bis-ns-CB[6] (140) and guest molecules.
Figure 103: The cucurbit[6]uril based complexes 141 for chiral discrimination.
Figure 104: Cucurbit[7]uril (131c) and its ferrocene guests (142) opposed.
Figure 105: Cucurbit[7]uril (131c) guest inclusion and representative guests.
Figure 106: Cucurbit[7]uril (131c) binding to succinylcholine (145) and different bis-ammonium and bis-phosphon...
Figure 107: Paraquat-cucurbit[8]uril complex 149.
Figure 108: Gluconuril-based ammonium receptors 150.
Figure 109: Examples of clefts (151a), tweezers (151b, 151c, 151d) and clips (151e).
Figure 110: Kemp’s triacid (152a), on example of Rebek’s receptors (152b) and guests.
Figure 111: Amino acid receptor (154) by Rebek et al.
Figure 112: Hexagonal lattice designed hosts by Bell et al.
Figure 113: Bell’s amidinium receptor (156) and the amidinium ion (157).
Figure 114: Aromatic phosphonic acids.
Figure 115: Xylene phosphonates 159 and 160a/b for recognition of amines and amino alcohols.
Figure 116: Bisphosphonate recognition motif 161 for a colorimetric assay with alizarin complexone (163) for ca...
Figure 117: Bisphosphonate/phosphate clip 164 and bisphosphonate cleft 165.
Figure 118: N-Methylpyrazine 166a, N-methylnicotinamide iodide (166b) and NAD+ (166c).
Figure 119: Bisphosphate cavitands.
Figure 120: Bisphosphonate 167 of Schrader and Finocchiaro.
Figure 121: Tweezer 168 for noradrenaline (80b).
Figure 122: Different tripods and heparin (170).
Figure 123: Squaramide based receptors 172.
Figure 124: Cage like NH4+ receptor 173 of Kim et al.
Figure 125: Ammonium receptors 174 of Chin et al.
Figure 126: 2-Oxazolin-based ammonium receptors 175a–d and 176 by Ahn et al.
Figure 127: Racemic guest molecules 177.
Figure 128: Tripods based on a imidazole containing macrocycle (178) and the guest molecules employed in the st...
Figure 129: Ammonium ion receptor 180.
Figure 130: Tetraoxa[3.3.3.3]paracyclophanes 181 and a cyclophanic tetraester (182).
Figure 131: Peptidic bridged paraquat-cyclophane.
Figure 132: Shape-selective noradrenaline host.
Figure 133: Receptor 185 for binding of noradrenaline on surface layers from Schrader et al.
Figure 134: Tetraphosphonate receptor for binding of noradrenaline.
Figure 135: Tetraphosphonate 187 of Schrader and Finocchiaro.
Figure 136: Zinc-Porphyrin ammonium-ion receptors 188 and 189 of Mizutani et al.
Figure 137: Zinc porphyrin receptor 190.
Figure 138: Zinc porphyrin receptors 191 capable of amino acid binding.
Figure 139: Zinc-porphyrins with amino acid side chains for stereoinduction.
Figure 140: Bis-zinc-bis-porphyrin based on Tröger’s base 193.
Figure 141: BINAP-zinc-prophyrin derivative 194 and it’s guests.
Figure 142: Bisaryl-linked-zinc-porphyrin receptors.
Figure 143: Bis-zinc-porphyrin 199 for diamine recognition and guests.
Figure 144: Bis-zinc-porphyrin crown ether 201.
Figure 145: Bis-zinc-porphyrin 202 for stereodiscrimination (L = large substituent; S = small substituent).
Figure 146: Bis-zinc-porphyrin[3]rotaxane and its copper complex and guests.
Figure 147: Dien-bipyridyl ligand 206 for co-ordination of two metal atoms.
Figure 148: The ligand and corresponding tetradentate co-complex 207 serving as enantioselective receptor for a...
Figure 149: Bis(oxazoline)–copper(II) complex 208 for the recognition of amino acids in aqueous solution.
Figure 150: Zinc-salen-complexes 209 for the recognition tertiary amines.
Figure 151: Bis(oxazoline)–copper(II) 211 for the recognition of amino acids in aqueous solution.
Figure 152: Zn(II)-complex of a C2 terpyridine crown ether.
Figure 153: Displacement assay and receptor for aspartate over glutamate.
Figure 154: Chiral complex 214 for a colorimetric displacement assay for amino acids.
Figure 155: Metal complex receptor 215 with tripeptide side arms.
Figure 156: A sandwich complex 216 and its displaceable dye 217.
Figure 157: Lanthanide complexes 218–220 for amino acid recognition.
Figure 158: Nonactin (221), valinomycin (222) and vancomycin (223).
Figure 159: Monesin (224a) and a chiral analogue for enantiodiscrimination of ammonium guests (224b).
Figure 160: Chiral podands (226) compared to pentaglyme-dimethylether (225) and 18-crown-6 (4).
Figure 161: Lasalocid A (228).
Figure 162: Lasalocid derivatives (230) of Sessler et al.
Figure 163: The Coporphyrin I tetraanion (231).
Figure 164: Linear and cyclic peptides for ammonium ion recognition.
Figure 165: Cyclic and bicyclic depsipeptides for ammonium ion recognition.
Figure 166: α-Cyclodextrin (136a) and novocaine (236).
Figure 167: Helical diol receptor 237 by Reetz and Sostmann.
Figure 168: Ammonium binding spherand by Cram et al. (238a) and the cyclic[6]metaphenylacetylene 238b in compar...
Figure 169: Receptor for peptide backbone and ammonium binding (239).
Figure 170: Anion sensor principle with 3-hydroxy-2-naphthanilide of Jiang et al.
Figure 171: 7-bromo-3-hydroxy-N-(2-hydroxyphenyl)naphthalene 2-carboxamide (241) and its amine binding.
Figure 172: Naturally occurring catechins with affinity to quaternary ammonium ions.
Figure 173: Spiropyran (244) and merocyanine form (244a) of the amino acid receptors of Fuji et al.
Figure 174: Coumarin aldehyde (245) and its iminium species with amino acid bound (245a) by Glass et al.
Figure 175: Coumarin aldehyde appended with boronic acid.
Figure 176: Quinolone aldehyde dimers by Glass et al.
Figure 177: Chromogenic ammonium ion receptors with trifluoroacetophenone recognition motifs.
Figure 178: Chromogenic ammonium ion receptor with trifluoroacetophenone recognition motif bound on different m...
Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
- Wei Jiang and
- Christoph A. Schalley
Beilstein J. Org. Chem. 2010, 6, No. 14, doi:10.3762/bjoc.6.14
- of guest from secondary dibenzylammonium hexafluorophosphate (360 M−1, 1.0 mM, in acetone-d6) [31] to the anthracenyl methyl-substituted analogue 5-H•PF6 (496 M−1, 1.0 mM, in acetone-d6) [26] increases the binding affinity with DB24C8, which is mainly attributed to stronger π-π stacking interactions
- reasons for this remarkable difference between C7 and the larger analogue dibenzo-24-crown-8. (i) According to related crystal structures [23][24][25], no π-π stacking interactions operate between hosts C7 or 4 and guests 6-H•PF6 or 7-H•PF6. (ii) Even more important, however, are the polarized methylene
Graphical Abstract
Scheme 1: Two synthetic procedures for the preparation of benzo-21-crown-7 (C7) and its formyl analogue 4: To...
Scheme 2: Molecular structures of guests 5-H•PF6, 6-H•PF6, and 7-H•PF6, and their complexes with 2-(n), C7 an...
Figure 1: 1H NMR spectra (500 MHz, 298 K, CDCl3:CD3CN = 2:1, 10.0 mM) of 5-H•PF6 (a), mixture of 5-H•PF6 and ...
Figure 2: ESI-FTICR mass spectrum of a mixture of 5-H•PF6 and 2-(n) in dichloromethane.
Figure 3: 1H NMR spectra (500 MHz, 298 K, CDCl3, 10.0 mM) of (a) C7, (b) C7 in the presence of 1 eq. KPF6, (c...
Figure 4: 1H NMR spectra (500 MHz, 298 K, CDCl3:CD3CN = 2:1, 10.0 mM) of (a) 6-HoPF6, (b) mixture of 6-HoPF6 ...
Figure 5: 1H NMR spectra (500 MHz, 298 K, CDCl3:CD3CN = 2:1, 10.0 mM) of (a) 6-H•PF6, equimolar mixtures of (b...
The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one
- Zhihua Wang,
- Sheng Zhu,
- Jianwu Shi and
- Hua Wang
Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55
- °. Using the middle benzene ring as a reference, the inner (C(5), C(6), C(7), C(12), C(13), and C(18)) helix increases by 1.46 Å and turns in-plane by 237.0° [22][23]. The crystal packing structure of 1 (Figure 3) is based on π-stacking along the a-axis in which the plane-to-plane distance is ca. 3.857 Å
Graphical Abstract
Figure 1: Chemical structures of 1 and 2.
Scheme 1: Synthetic route to 1 and 2. Reagents and conditions: (a) (i) n-BuLi (2.3 equiv), Et2O, reflux; (ii)...
Figure 2: Molecular structure and conformation of 1.
Figure 3: Crystal packing structure of 1.
Figure 4: UV–vis spectra of 1 and 2 in chloroform ([C] = 1 × 10−5 M).
Quinoline based receptor in fluorometric discrimination of carboxylic acids
- Kumaresh Ghosh,
- Suman Adhikari,
- Asoke P. Chattopadhyay and
- Purnendu Roy Chowdhury
Beilstein J. Org. Chem. 2008, 4, No. 52, doi:10.3762/bjoc.4.52
- ring protons (Figure 14) during complexation with citric acid. The quinoline ring protons (marked with asterisks in Figure 14) suffer a downfield shift upon complexation and led us to presume a weak edge to face type π-stacking interaction between the pendant quinolines. Theoretical calculations on
- interaction brings the pendant quinolines close to exhibit a weak edge to face π-stacking interaction showing the shortest possible distance of 3.48 Å. The hydrogen bond distances are listed in Figure 15a. In comparison, this weak π-stacking interaction between the quinolines is no longer found in the complex
- the cleft with a number of hydrogen bonds and the pendant naphthalenes are separated by a large distance with no π-stacking interaction between them. This is in accordance with the experimental results, shown in the fluorescence experiment. Conclusion We have discussed the synthesis and sensing
Graphical Abstract
Figure 1: Structures of compounds 1 and 2.
Scheme 1: Syntheses of receptors 1 and 2.
Figure 2: UV-vis spectra of 1 (c = 5.05 × 10−5 M) in different solvents.
Figure 3: UV-vis spectra of 2 (c = 5.05 × 10−5 M) in different solvents.
Figure 4: UV spectra of the complex of 1 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 5: UV spectra of the complex of 1 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 6: UV spectra of the complex of 2 with citric acid (c = 1.67 × 10−5 M) and its change of absorbance on...
Figure 7: UV spectra of the complex of 2 with D-(−)-tartaric acid (c = 1.67 × 10−5 M) and its change of absor...
Figure 8: Fluorescence change of 1 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 9: Plot of the ratio of excimer to monomer emission vs concentration of the complex of 1 with citric a...
Figure 10: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of citric acid dissolved in CHCl...
Figure 11: Fluorescence change of 1 in CHCl3 (c = 1.67 × 10−5 M) upon addition of D-(−)-tartaric acid dissolve...
Figure 12: Fluorescence change of 2 in CHCl3 in the presence of carboxylic acids (λex = 290 nm).
Figure 13: Fluorescence change of 2 in CHCl3 (c = 1.67 × 10−5 M) upon addition citric acid dissolved in CHCl3 ...
Figure 14: 1H NMR (in CDCl3) spectra of receptor 1 (c = 3.57 × 10−3 M; bottom) and the 1:1 complex with citric...
Figure 15: AM1 optimized geometries of the complexes of 1 with (a) citric acid, hydrogen bond distances: a = 2...
Figure 16: AM1 optimized geometry of the complex of 2 with citric acid, hydrogen bond distances: a = 2.12 Å, b...
Inversion symmetry and local vs. dispersive interactions in the nucleation of hydrogen bonded cyclic n-mer and tape of imidazolecarboxamidines
- Sihui Long,
- Venkatraj Muthusamy,
- Peter G. Willis,
- Sean Parkin and
- Arthur Cammers
Beilstein J. Org. Chem. 2008, 4, No. 23, doi:10.3762/bjoc.4.23
- aromatic substituents at R2 in 8a and 8b and at R3 in 8b. Optimizing π-stacking, hydrogen bonding and θ likely allowed these two C1 dimer solid states in lieu of the otherwise ubiquitous Ci dimer. There were three other imidazolecarboxamidines in this study that did not crystallize as dimers: trimer 6b
- . The high-energy molecular component in C1 dimer 8b (high-energy red diamond in Figure 11) corresponded to the highest-energy θ angle in Figure 8 that lost π resonance between the amidine and the imidazole moiety. As discussed earlier, this structure is likely a result of extensive π-stacking
Graphical Abstract
Figure 1: 1: An intuitive prediction regarding the relationship between crude hydrogen bond donor/acceptor di...
Figure 2: Facile syntheses of imidazole carboxamidines from commercial imidazoles and carbodiimides furnished...
Figure 3: The NCNC dihedral angle, θ, between the hydrogen bond donors and acceptors, was assigned values bet...
Figure 4: Stereoview of Dimer 5c. This dimer stacked imidazole rings with R1 pointing in opposite directions.
Figure 5: Stereoview of trimer 6b.
Figure 6: Stereoview of tetramer 9a.
Figure 7: Stereoview of linear hydrogen bond tape 11a.
Figure 8: The calculated (rhf/6-311+g(d,p)) potential energy (kcal/mol) of N,N'-dimethyl-1H-imidazole-1-carbo...
Figure 9: A Flow chart for the calculation of the energies of the n-mers minus the effects of packing and sub...
Figure 10: Icons correspond to those in Figure 8. Crosses indicate structures with aromatic groups. The calculated (rh...
Figure 11: The icon legend is identical to Figure 8 and Figure 10. The Y-axis from Figure 8 energies (θ only) and the X-axis from Figure 10 ener...
Crystal engineering of analogous and homologous organic compounds: hydrogen bonding patterns in trimethoprim hydrogen phthalate and trimethoprim hydrogen adipate
- Packianathan Thomas Muthiah,
- Savarimuthu Francis,
- Urszula Rychlewska and
- Beata Warżajtis
Beilstein J. Org. Chem. 2006, 2, No. 8, doi:10.1186/1860-5397-2-8
- leading to base-pairing, quadruple hydrogen bonded arrays, DDAA and DADA (D- donor, A = acceptor), etc. C-H...π, π-π stacking, etc are further stabilizing the crystal structures. The quadruple hydrogen bonded arrays have been observed in the crystal structures of TMP m-chlorobenzoate, [11] TMP-sorbate
Graphical Abstract
Figure 1: The schematic diagram for the various hydrogen-bonded motifs observed in compound (1).
Figure 2: The schematic diagram for the various hydrogen-bonded motifs observed in compound (2).
Figure 3: The ORTEP 3 view of the asymmetric unit of the compound 1.
Figure 4: The ORTEP 3 view of the asymmetric unit of the compound 2.
Figure 5: The hydrogen-bonded supramolecular ladder in the compound 1.
Figure 6: The hydrogen-bonded DDAA array in the compound 2.
Figure 7: The supramolecular chain made up of hydrogen adipate in the compound 2.
Figure 8: Scatterplot illustrating the distribution of the two torsion angles (C4-C5-C7-C8 (TOR1) and C5-C7-C...
