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Hydrogen bond design principles

Overview

Lucas J. Karas, Chia‐Hua Wu, Ranjita Das, Judy I‐Chia Wu

Published Online: May 16 2020

DOI: 10.1002/wcms.1477

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Abstract Hydrogen bonding principles are at the core of supramolecular design. This overview features a discussion relating molecular structure to hydrogen bond strengths, highlighting the following electronic effects on hydrogen bonding: electronegativity, steric effects, electrostatic effects, π‐conjugation, and network cooperativity. Historical developments, along with experimental and computational efforts, leading up to the birth of the hydrogen bond concept, the discovery of nonclassical hydrogen bonds (CH…O, OH…π, dihydrogen bonding), and the proposal of hydrogen bond design principles (e.g., secondary electrostatic interactions, resonance‐assisted hydrogen bonding, and aromaticity effects) are outlined. Applications of hydrogen bond design principles are presented. This article is categorized under: Structure and Mechanism > Molecular Structures Structure and Mechanism > Reaction Mechanisms and Catalysis

(a) Schematic illustration of dihydrogen bonding. Dihydrogen bonds were shown to direct the (b) preassembly of covalent materials, and (c) the diastereoselectivity of borohydride reduction

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(a) Schematic illustration of XH…π interactions. (b) and (c) Examples of OH…π hydrogen bonding. (d) Example of BH…π hydrogen bonding

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(a) Schematic illustration of CH…Y interactions (Y = electronegative atom or anion). (b) F₂CH…O hydrogen bonding. (c) Examples of anion receptors based on CH…anion interactions

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Effects of electronegativity on OH…N vs. NH…N hydrogen bond strength. Explanations based on: (a) donor–acceptor orbital interactions (using water…ammonia and ammonia…ammonia as examples), and (b) dipole–dipole interactions

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Depictions of hydrogen bonding, in (a) H₂OH₂O and (b) ammonium hydroxide, based on the early works of Latimer and Rodebush¹

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Timeline for the development of hydrogen bond design principles

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(a) Hydrogen bonding networks in the active site of triosephosphate isomerase. (b) Cooperative hydrogen bonds can stabilize the conjugate base of OH substituted benzoic acid (note pK_a values for the acid). (c) Example of a covalent polyol system. (d) Enhanced hydrogen bonding resulting from neutral, short‐range networks (see OH group in bold)

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(a) Aromaticity gain and loss in hydrogen‐bonded heterocycles, and (b) a reversed effect in photoexcited states

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Resonance structures showing the effects of aromaticity gain in (a) tropolone, and in hydrogen‐bonded (b) squaramide and C) guanine

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(a) Intramolecular and intermolecular resonance‐assisted hydrogen bonding (RAHB) in β‐diketone. (b) Possible RAHB effects in hydrogen‐bonded dimers and base pairs

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Examples of quadruply hydrogen bonded arrays prepared based on the secondary electrostatic interaction (SEI) model. (a) 2‐Ureido‐4‐pyrimidone,⁶⁷ and (b) Blight's AAAA‐DDDD array⁶⁸

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Secondary electrostatic interactions (SEIs) between proton donors (“D,” in orange) and acceptors (“A,” in blue) in: (a) doubly, (b) triply, and (c) quadruply hydrogen bonded arrays. Solid lines indicate attractive interactions and dashed lines indicate repulsive interactions

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Examples of other diamine‐based proton sponges: TMGN, P₂‐TPPN, t‐Bu–P₂, vinamidine, and a fluorene‐based proton sponge

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(a) The original “proton sponge,” DMAN. (b) Protonation of the diamine relieves lone pair repulsion, resulting in low‐barrier [N…H…N]⁺ hydrogen bonding

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References

Latimer, WM, Rodebush, WH. Polarity and ionization from the standpoint of the Lewis theory of valence. J Am Chem Soc. 1920;42(7):1419–1433.
Jeffrey, GA. An introduction to hydrogen bonding. New York and Oxford: Oxford University Press, 1997.
Lewis, GN. Valence and the structure of atoms and molecules. New York, NY: Chemical Catalog Co., 1923 p. 109.
Watson, JD, Crick, FHC. Molecular structure of nucleic acids: A structure for deoxyribose nucleic acid. Nature. 1953;171:737–738.
Pauling, L, Corey, RB, Branson, HR. The structure of proteins: Two hydrogen bonded helical configurations of the polypeptide chain. Proc Natl Acad Sci USA. 1951;37(4):205–211.
Pauling, L, Corey, RB. The pleated sheet, a new layer configuration of polypeptide chains. Proc Natl Acad Sci USA. 1951;37(5):251–256.
Huggins, ML. Hydrogen bridges in organic compounds. J Org Chem. 1936;1(5):407–456.
Weinhold, F, Landis, CR. Valency and bonding: A natural bond orbital donor–acceptor perspective. Cambridge, UK: Cambridge University Press, 2005.
Coulson, CA. The hydrogen bond–a review of the present position. Research. 1957;10:149–159.
Pimentel, GC. The bonding of trihalide and bifluoride ions by the molecular orbital method. J Chem Phys. 1951;19(4):446–448.
Rundle, RE. Coordination number and valence in modern structural chemistry. Rec Prog Chem. 1962;23(1962):195–221.
Coulson, CA. The nature of the bonding in xenon fluorides and related molecules. J Chem Soc. 1964;1442–1454.
Munzarová, ML, Hoffman, R. Electron‐rich three‐center bonding: Role of s, p interactions across the p‐block. J Am Chem Soc. 2002;124(17):4785–4795.
Nemes, CT, Laconsay, CJ, Galbraith, JM. Hydrogen bonding from a valence bond theory perspective: The role of covalency. Phys Chem Chem Phys. 2018;20(32):20963–20969.
Pauling, L. The nature of the chemical bond. 3rd ed. Ithaca, NY: Cornell University Press, 1960.
Donohue, J. The hydrogen bond in organic crystals. J Phys Chem A. 1952;56(4):502–510.
Etter, MC. A new role for the hydrogen‐bond acceptors in influencing packing patterns of carboxylic acids and amids. J Am Chem Soc. 1982;104(4):1095–1096.
Etter, MC. Encoding and decoding hydrogen‐bond patterns of organic compounds. Acc Chem Res. 1990;23(4):120–126.
Gerlt, JA, Gassman, PG. An explanation for rapid enzyme‐catalyzed proton abstraction from carbon acids: Importance of late transition states in concerted mechanisms. J Am Chem Soc. 1993;115(24):11552–11568.
Gerlt, JA, Gassman, PG. Understanding the rates of certain enzyme‐catalyzed reactions: Proton abstraction from carbon acids, acyl transfer reactions, and displacement reactions of phosphodiesters. Biochemistry. 1993;32(45):11934–11952.
Cleland, WW, Kreevoy, MM. Low‐barrier hydrogen bonds and enzyme catalysis. Science. 1994;264(5167):1887–1890.
Frey, PA, Witt, SA, Tobin, JB. A low‐barrier hydrogen bond in the catalytic triad of serine protease. Science. 1994;264(5167):1927–1930.
Graham, JD, Buytendyk, AM, Wang, D, Bowen, KH, Collins, KD. Strong, low‐barrier hydrogen bonds may be available to enzymes. Biochemistry. 2014;53(2):344–349.
Perrin, CL. Are short, low‐barrier hydrogen bonds unusually strong? Acc Chem Res. 2010;43(12):1550–1557.
Guthrie, JP. Short strong hydrogen bonds: Can they explain enzyme catalysis? Chem Biol. 1996;3(3):163–170.
Perrin, CL, Nielson, JB. Strong hydrogen bonds in chemistry and biology. Annu Rev Phys Chem. 1997;48:511–544.
Pimentel, GC, McClellan, AL. The hydrogen bond. Freeman, San Francisco and London: W. H, 1960.
Sutor, DJ. The C–H… O hydrogen bond in crystals. Nature. 1962;195:68–69.
Sutor, DJ. Evidence for the existence of C–H⋯O hydrogen bonds in crystals. J Chem Soc. 1963;0:1105–1110.
Structural, DJ. Chemistry and molecular biology. San Francisco, CA: A. Rich and N. Davidson, W. H. Freeman, 1968;p. 443–465.
Taylor, R, Kennard, O. Crystallographic evidence for the existence of C–H⋯O, C–H⋯N, and C–H⋯cl hydrogen bonds. J Am Chem Soc. 1982;104(19):5063–5070.
Gu, Y, Kar, T, Scheiner, S. Fundamental properties of the CH···O interaction: Is it a true hydrogen bond? J Am Chem Soc. 1999;121(40):9411–9422.
Scheiner, S. Weak H‐bonds. Comparisons of CH⋯O to NH⋯O in proteins and PH⋯N to direct P⋯N interactions. Phys Chem Chem Phys. 2011;13(31):13860–13872.
Desiraju, GR, Steiner, T. The weak hydrogen bond: In structural chemistry and biology. Oxford, UK: Oxford University Press, 1999.
Desiraju, GR. The C−H···O hydrogen bond: Structural implications and supramolecular design. Acc Chem Res. 1996;29(9):441–449.
Sessler, CD, Rahm, M, Becker, S, Goldberg, JM, Wang, F, Lippard, SJ. CF₂H, a hydrogen bond donor. J Am Chem Soc. 2017;139(27):9325–9332.
Eytel, LM, Fargher, HA, Haley, MM, Johnson, DW. The road to aryl C–H…anion binding was paved with good intentions: Fundamental studies, host design, and historical perspectives in CH hydrogen bonding. Chem Commun. 2019;55(36):5159–5206.
Yoon, D‐W, Gross, DE, Lynch, VM, Sessler, JL, Hay, BP, Lee, C‐H. Phenyl‐, pyrrole‐, and furan‐containing diametrically strapped calix[4]pyrroles. An experimental and theoretical study of hydrogen bonding effects in chloride anion recognition. Angew Chem Int Ed. 2008;47(27):5038–5042.
Li, Y, Flood, AH. Strong, size‐selective, and electronically tunable C–H…halide binding with steric control over aggregation from synthetically modular, shape‐persistent [3₄]Trazolophanes. J Am Chem Soc. 2008;130(36):12111–12122.
Treseca, BW, Zakharov, LN, Carroll, CN, Johnson, DW, Haley, MM. Aryl C–H…cl⁻ hydrogen bonding in a fluorescent anion sensor. Chem Commun. 2013;49(65):7240–7242.
Meyer, EA, Castellano, RK, Diederich, F. Interactions with aromatic rings in chemical and biological recognition. Angew Chem Int Ed. 2003;42(11):1210–1250.
West, R. Hydrogen bonding of phenols to olefins. J Am Chem Soc. 1959;81(7):1614–1617.
Suziki, S, Green, PG, Bumgarner, RR, Dasgupta, S, Goddard, WA III, Blake, GA. Benzene forms hydrogen bonds with water. Science. 1992;257(5072):942–945.
Nishio, M. CH/π hydrogen bonds in crystals. CrstEngComm. 2004;6(27):130–158.
Nishio, M. The CH/π hydrogen bond in chemistry. Conformation, supramolecules, optical resolution and interactions involving carbohydrates. Phys Chem Chem Phys. 2011;13(31):13873–13900.
Harigai, M, Kataoka, M, Imamoto, Y. A single CH/π weak hydrogen bond governs stability and the photocycle of the photoactive yellow protein. J Am Chem Soc. 2006;128(33):10646–10647.
Zhang, X, Dai, H, Yan, H, Zou, W, Cremer, D. B–H···π interaction: A new type of nonclassical hydrogen bonding. J Am Chem Soc. 2016;138(13):4334–4337.
Crabtree, RH. A new type of hydrogen bond. Science. 1998;282(5396):2000–2001.
Crabtree, RH, Siegbahn, PE, Eisenstein, O, Rheingold, AL, Koetzle, TF. A new intermolecular interaction: Unconventional hydrogen bonds with element−hydride bonds as proton acceptor. Acc Chem Res. 1996;29(7):348–354.
Custelcean, R, Jackson, JE. Dihydrogen bonding: Structures, energetics, and dynamics. Chem Rev. 2001;101(7):1963–1980.
Custelcean, R, Jackson, JE. Topochemical control of covalent bond formation by dihydrogen bonding. J Am Chem Soc. 1998;120(49):12935–12941.
Gatling, SC, Jackson, JE. Reactivity control via dihydrogen bonding: Diastereoselection in borohydride reductions of α‐hydroxyketones. J Am Chem Soc. 1999;121(37):8655–8656.
Yang, L, Hubbard, TA, Cockroft, SL. Can non‐polar hydrogen atoms accept hydrogen bonds? Chem Commun. 2014;50(40):5212–5214.
Echeverría, J, Aullón, G, Danovich, D, Shaik, S, Alvarez, S. Dihydrogen contacts in alkanes are subtle but not faint. Nat Chem. 2011;3(4):323–330.
Echeverría, J, Aullón, G, Alvarez, S. Dihydrogen intermolecular contacts in group 13 compounds: H…H or E…H (E = B, Al, Ga) interactions? Dalton Trans. 2017;46(9):2844–2854.
Alder, RW, Bowman, PS, Steele, WRS, Winterman, DR. The remarkable basicity of 1,8‐bis(dimethylamino)naphthalene. Chem Comm. 1968;13:723–724.
Staab, HA, Saupe, T. “Proton sponges” and the geometry of hydrogen bonds: Aromatic nitrogen bases with exceptional basicities. Angew Chem Int Ed. 1988;27(7):865–879.
Alder, RW. Strain effects on amine basicities. Chem Rev. 1989;89(5):1215–1223.
Raab, V, Kipke, J, Gschwind, RM, Sundermeyer, J. 1,8‐Bis(tetramethylguanidino)naphthalene (tmgn): A new, superbasic and kinetically active “proton sponge”. Chem A Eur J. 2002;8(7):1682–1693.
Raab, V, Gauchenova, E, Merkoulov, A, et al. 1,8‐Bis(hexamethyltriaminophosphazenyl)naphthalene, HMPN: A superbasic bisphosphazene “proton sponge”. J Am Chem Soc. 2005;127(45):15738–15743.
Kögel, JF, Oelkers, B, Kovačević, B, Sundermeyer, J. A new synthetic pathway to the second and third generation of superbasic bisphosphazene proton sponges: The run for the best chelating ligand for a proton. J Am Chem Soc. 2013;135(47):17768–17774.
Schwesinger, R, Schlemper, H, Hasenfratz, C, et al. Extremely strong, uncharged auxiliary bases; monomeric and polymer‐supported polyaminophosphazenes (P₂–P₅). Liebigs Ann. 1996;1996(7):1055–1081.
Schwesinger, R, Mibfeldt, DCM, Peter, K, Schnering, HGV. Novel, very strongly basic, pentacyclic “proton sponges“ with vinamidine structure. Angew Chem Int Ed. 1987;26(11):1165–1167.
Staab, HA, Saupe, T, Krieger, C. 4,5‐Bis(demethylamino)fluorene, a new “proton sponge”. Angew Chem Int Ed. 1983;22(9):731–732.
Jorgensen, WL, Pranata, J. Importance of secondary interactions in triply hydrogen bonded complexes: Guanine–cytosine vs. uracil‐2,6‐diaminopyridine. J Am Chem Soc. 1990;112(5):2008–2010.
Pranata, J, Wierschke, SG, Jorgensen, WL. OPLS potential functions for nucleotide bases. Relative association constants of hydrogen‐bonded base pairs in chloroform. J Am Chem Soc. 1991;113(8):2810–2819.
Sijbesma, RP, Beijer, FH, Brunsveld, L, et al. Reversible polymers formed from self‐complementary monomers using quadruple hydrogen bonding. Science. 1997;278(5343):1601–1604.
Blight, BA, Hunter, CA, Leigh, DA, McNab, H, Thomson, PI. An AAAA–DDDD quadruple hydrogen‐bond array. Nat Chem. 2011;3(3):244–248.
Sartorius, J, Schneider, HJ. A general scheme based on empirical increments for the prediction of hydrogen‐bond associations of nucleobases and of synthetic host–guest complexes. Chem A Eur J. 1996;2(11):1446–1452.
Corbin, PS, Zimmerman, SC. Self‐association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen‐bonded dimers. J Am Chem Soc. 1998;120(37):9710–9711.
Tiwari, MK, Vanka, K. Exploiting directional long‐range secondary forces for regulating electrostatics‐dominated noncovalent interactions. Chem Sci. 2017;8(2):1378–1390.
Popelier, PLA, Joubert, L. The elusive atomic rationale for DNA base pair stability. J Am Chem Soc. 2002;124(29):8725–8729.
Lukin, O, Leszczynski, J. Rationalizing the strength of hydrogen‐bonded complexes. Ab initio HF and DFT studies. J Phys Chem A. 2002;106(29):6775–6782.
Fonseca Guerra, C, Bickelhaupt, FM, Snijders, JG, Baerends, EJ. The nature of the hydrogen bond in DNA base pairs: The role of charge transfer and resonance assistance. Chem A Eur J. 1999;5(12):3581–3594.
Guillaumes, L, Simon, S, Fonseca, GC. The role of aromaticity, hybridization, electrostatics, and covalency in resonance‐assisted hydrogen bonds of adenine–thymine (AT) base pairs and their mimics. ChemistryOpen. 2015;4(3):318–327.
van der Lubbe, SCC, Fonseca, GC. Hydrogen‐bond strength of CC and GG pairs determined by steric repulsion: Electrostatics and charge transfer overruled. Chem A Eur J. 2017;23(43):10249–10253.
Zarycz, M, Natalia, C, Fonseca, GC. NMR 1H‐shielding constants of hydrogen‐bond donor reflect manifestation of the Pauli principle. J Phys Chem Lett. 2018;9(13):3720–3724.
Wu, CH, Zhang, Y, van Rickley, K, Wu, JI. Aromaticity gain increases the inherent association strengths of multipoint hydrogen‐bonded arrays. Chem Comm. 2018;54(28):3512–3515.
Zhang, Y, Wu, CH, Wu, JI. Why do A·T and G·C self‐sort? Hückel aromaticity as a driving force for electronic complementarity in base pairing. Org Biomol Chem. 2019;17(7):1881–1885.
Paudel, H, Das, R, Wu, CH, Wu, JI. Self‐assembling quartets: How do π‐conjugation patterns affect resonance‐assisted hydrogen bonding? Org Biomol Chem. 2020;18(6):1078–1081.
Narváez, WEV, Jiménez, EI, Romero‐Montalvo, E, et al. Acidity and basicity interplay in amide and imide self‐association. Chem Sci. 2018;9(19):4402–4413.
Narváez, WEV, Jiménez, EI, Cantú‐Reyes, M, Yatsimirsky, AK, Hernández‐Rodríguez, M, Rocha‐Rinza, T. Stability of doubly and triply H‐bonded complexes governed by acidity–basicity relationships. Chem Comm. 2019;55(11):1556–1559.
van der Lubbe, SCC, Zaccaria, F, Sun, X, Fonseca, GC. Secondary electrostatic interaction model revised: Prediction comes mainly from measuring charge accumulation in hydrogen‐bonded monomers. J Am Chem Soc. 2019;141(12):4878–4885.
Gilli, G, Bullucci, F, Ferretti, V, Bertolasi, V. Evidence for resonance‐assisted hydrogen bonding from crystal‐structure correlations on the enol form of the β‐diketone fragment. J Am Chem Soc. 1989;111(3):1023–1028.
Gilli, P, Bertolasi, V, Ferretti, V, Gilli, G. Covalent nature of the strong homonuclear hydrogen‐bond‐study of the O‐H—O system by crystal‐structure correlation methods. J Am Chem Soc. 1994;116(3):909–915.
Bertolasi, V, Gilli, P, Ferretti, V, Gilli, G. Evidence for resonance‐assisted hydrogen bonding. 2. Intercorrelation between crystal structure and spectroscopic parameters in eight intramolecularly hydrogen bonded 1,3‐diaryl‐1,3‐propanedione enols. J Am Chem Soc. 1991;113(13):4917–4925.
Bertolasi, V, Gilli, P, Ferretti, V, Gilli, G. Resonance‐assisted O‐H…O hydrogen bonding: Its role in the crystalline self‐recognition of β‐diketone enols and its structural and IR characterization. Chem A Eur J. 1996;2(8):925–934.
Zhou, Y, Deng, G, Zheng, YZ, Xu, J, Ashraf, H, Yu, ZW. Evidences for cooperative resonance‐assisted hydrogen bonds in protein secondary structure analogs. Scient Rep 2016;6:36932(1–8).
Gora, RW, Maj, M, Grabowski, SJ. Resonance‐assisted hydrogen bonds revisited. Resonance stabilization vs. charge delocalization. Phys Chem Chem Phys. 2013;15(7):2514–2522.
Grosch, AA, van der Lubbe, SCC, Fonseca, GC. Nature of intramolecular resonance assisted hydrogen bonding in malonaldehyde and its saturated analogue. J Phys Chem A. 2018;122(6):1813–1820.
Alkorta, I, Elguero, J, Mo, O, Yanez, M, Bene, JED. Are resonance‐assisted hydrogen bonds ‘resonance assisted’? A theoretical NMR study. Chem Phys Lett. 2005;411(4–6):411–415.
Jiang, X, Zhang, H, Wu, W, Mo, Y. A critical check for the role of resonance in intramolecular hydrogen bonding. Chem A Eur J. 2017;23(66):16885–16891.
Sobczyk, L, Grabowski, SJ, Krygowski, TM. Interrelation between H‐bond and π‐electron delocalization. Chem Rev. 2005;105(10):3513–3560.
Mahmudov, KT, Pombeiro, AJL. Resonance‐assisted hydrogen bonding as a driving force in synthesis and a synthon in the design of materials. Chem A Eur J. 2016;22(46):16356–16398.
Dewar, MJS. Structure of stipitatic acid. Nature. 1945;155(3924):50–51.
Stasyuk, OA, Szatyłowicz, H, Krygowski, TM. Effect of H‐bonding and complexation with metal ions on the π‐electron structure of adenine tautomers. Org Biomol Chem. 2014;12(3):456–466.
Cyranśki, MK, Gilski, M, Jaskoĺski, M, Krygowski, TM. On the aromatic character of the heterocyclic bases of DNA and RNA. J Org Chem. 2003;68(22):8607–8613.
Maksić, ZB, Glasovac, Z, Despotović, I. Predicted high proton affinity of poly‐2, 5‐dihydropyrrolimines—The aromatic domino effect. J Phys Org Chem. 2002;15(8):499–508.
Maksić, ZB, Kovacěvić, B. Spatial and electronic structure of highly basic organic molecules: Cyclopropeneimines and some related systems. J Phys Chem A. 1999;103(33):6678–6684.
Krygowski, TM, Szatyłowicz, H, Zachara, JE. How H‐bonding modifies molecular structure and π‐electron delocalization in the ring of pyridine/pyridinium derivatives involved in H‐bond complexation. J Org Chem. 2005;70(22):8859–8865.
Szatyłowicz, H, Krygowski, TM, Zachara, JE. Long‐distance structural consequences of H‐bonding. How H‐bonding affects aromaticity of the ring in variously substituted aniline/anilinium/anilide complexes with bases and acids. J Chem Inf Model. 2007;47(3):875–886.
Quiñonero, D, Prohens, R, Garau, C, et al. A theoretical study of aromaticity in squaramide complexes with anions. Chem Phys Lett. 2002;351(1–2):115–120.
Quiñonero, D, Frontera, A, Ballester, P, Deyà, PM. A theoretical study of aromaticity in squaramide and oxocarbons. Tetrahedron Lett. 2000;41(12):2001–2005.
Wu, JI, Jackson, JE, Schleyer, PR. Reciprocal hydrogen bonding–aromaticity relationships. J Am Chem Soc. 2014;136(39):13526–13529.
Kakeshpour, T, Wu, JI, Jackson, JE. AMHB:(anti) aromaticity‐modulated hydrogen bonding. J Am Chem Soc. 2016;138(10):3427–3432.
Kakeshpour, T, Bailey, JP, Jenner, MR, et al. High‐field NMR spectroscopy reveals aromaticity‐modulated hydrogen bonding in heterocycles. Angew Chem Int Ed. 2017;56(33):9842–9846.
Talens, VS, Englebienne, P, Trinh, TT, Noteborn, WEM, Voets, IK, Kieltyka, RE. Aromatic gain in a supramolecular polymer. Angew Chem Int Ed. 2015;54(36):10502–10506.
Anand, M, Fernandez, I, Schaefer, HF, Wu, JI. Hydrogen bond–aromaticity cooperativity in self‐assembling 4‐pyridone chains. J Comput Chem. 2016;37(1):59–63.
Wen, Z, Wu, JI. Antiaromaticity gain increases the potential for n‐type charge transport in hydrogen‐bonded π‐conjugated cores. Chem Comm. 2020;56(13):2008–2011.
Wu, CH, Ito, K, Buytendyk, AM, Bowen, KH, Wu, JI. Enormous hydrogen bond strength enhancement through π‐conjugation gain: Implications for enzyme catalysis. Biochemistry. 2017;56(33):4318–4322.
Wu, CH, Karas, LJ, Ottosson, H, Wu, JI. Excited‐state proton transfer relieves antiaromaticity in molecules. Proc Natl Acad Sci USA. 2019;116(41):20303–20308.
Baird, NC. Quantum organic photochemistry. II. Resonance and aromaticity in the lowest ³ππ* state of cyclic hydrocarbons. J Am Chem Soc. 1972;94(14):4941–4948.
Rosenberg, M, Dahlstrand, C, Kilså, H, Ottosson, H. Excited state aromaticity and antiaromaticity: Opportunities for photophysical and photochemical rationalizations. Chem Rev. 2014;114(10):5379–5425.
Sobolewski, AL, Domcke, W. Intramolecular hydrogen bonding in the S1(ππ*) excited state of anthranilic acid and salicylic acid: TDDFT calculation of excited‐state geometries and infrared spectra. J Phys Chem A. 2004;108(49):10917–10922.
Zhao, GJ, Han, KL. Early time hydrogen‐bonding dynamics of photoexcited coumarin 102 in hydrogen‐donating solvents: Theoretical study. J Phys Chem A. 2007;111(13):2469–2474.
Zhao, GJ, Han, KL. Ultrafast hydrogen bond strengthening of the photoexcited fluorenone in alcohols for facilitating the fluorescence quenching. J Phys Chem A. 2007;111(38):9218–9223.
Zhao, GJ, Han, KL. Effects of hydrogen bonding on tuning photochemistry: Concerted hydrogen‐bond strengthening and weakening. ChemPhysChem. 2008;9(13):1842–1846.
Zhao, GJ, Han, KL. Hydrogen bonding in the electronic excited state. Acc Chem Res. 2012;45(3):404–413.
Jencks, WP. Binding energy, specificity, and enzymic catalysis: The circe effect. Ad Enzymol. 1975;43:219–410.
Fierke, CA, Jencks, WP. Two functional domains of coenzyme a activate catalysis by coenzyme a transferase. Pantetheine and adenosine 3′‐phosphate 5′‐diphosphate. J Biol Chem. 1986;261(11):7603–7606.
Shan, SO, Loh, S, Herschlag, D. Energetic effects of multiple hydrogen bonds. Implications for enzyme catalysis. J Am Chem Soc. 1996;118(24):5515–5518.
Shokri, A, Schmidt, J, Wang, XB, Kass, SR. Hydrogen bonded arrays: The power of multiple hydrogen bonds. J Am Chem Soc. 2012;134(4):2094–2099.
Shokri, A, Wang, Y, O’Doherty, GA, Wang, XB, Kass, SR. Hydrogen‐bond networks: Strengths of different types of hydrogen bonds and an alternative to the low barrier hydrogen‐bond proposal. J Am Chem Soc. 2013;135(47):17919–17924.
Dominelli‐Whiteley, N, Brown, JJ, Muchowska, KB, et al. Short‐range cooperativity in hydrogen‐bond chains. Angew Chem Int Ed. 2017;56(26):7658–7662.
Kato, Y, Conn, MM, Rebek, J Jr. Hydrogen bonding in water using synthetic receptors. Proc Natl Acad Sci USA. 1995;92(4):1208–1212.
Jeong, KS, Rebek, J Jr. Molecular recognition: Hydrogen bonding and aromatic stacking converge to bind cytosine derivatives. J Am Chem Soc. 1988;110(10):3327–3328.
Huang, C‐Y, Cabell, LA, Anslyn, EV. Molecular recognition of cyclitols by neutral polyaza‐hydrogen‐bonding receptors: The strength and influence of intramolecular hydrogen bonds between vicinal alcohols. J Am Chem Soc. 1994;116(7):2778–2792.
Zimmerman, SC, VanZyl, CM, Hamilton, GS. Rigid molecular tweezers: Preorganized hosts for electron donor‐acceptor complexation in organic solvents. J Am Chem Soc. 1989;111(4):1373–1381.

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