Excited-state proton transfer relieves antiaromaticity in molecules
Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first ¹ππ* states, and proton transfer (either inter- or intramolecularly) hel...
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| Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 116; no. 41; pp. 20303 - 20308 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
National Academy of Sciences
08.10.2019
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first ¹ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o-Salicylic acid undergoes ESPT only in the “antiaromatic” S₁ (¹ππ*) state, but not in the “aromatic” S₂ (¹ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. |
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| AbstractList | Excited-state proton transfer (ESPT) is universally recognized as a reaction that relaxes the energy of a photoexcited organic compound. It is commonly found in many light-driven processes. Here we identify decisive principles underlying why and when ESPT happens. Our computational investigation of prototypical ESPT reactions finds that the occurrence of ESPT can be explained by an electron-counting rule—Baird’s rule, which remains largely ignored despite having a near–50-y-old history. We emphasize that this surprising connection not only explains the mechanistic principle of ESPT reactions, but it also predicts whether hydrogen bonding interactions that form within and between organic compounds might strengthen or weaken when irradiated by light. Recognizing this relationship has tremendous interpretive merit for organic photochemistry.
Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4
n
+ 2] π-aromatic in the ground state, become [4
n
+ 2] π-antiaromatic in the first
1
ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity.
o-
Salicylic acid undergoes ESPT only in the “antiaromatic” S
1
(
1
ππ*) state, but not in the “aromatic” S
2
(
1
ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4 n + 2] π-aromatic in the ground state, become [4 n + 2] π-antiaromatic in the first 1 ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o- Salicylic acid undergoes ESPT only in the “antiaromatic” S 1 ( 1 ππ*) state, but not in the “aromatic” S 2 ( 1 ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. Baird's rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first 1ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o-Salicylic acid undergoes ESPT only in the "antiaromatic" S1 (1ππ*) state, but not in the "aromatic" S2 (1ππ*) state. Stokes' shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird's rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first ¹ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o-Salicylic acid undergoes ESPT only in the “antiaromatic” S₁ (¹ππ*) state, but not in the “aromatic” S₂ (¹ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. Baird's rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4 + 2] π-aromatic in the ground state, become [4 + 2] π-antiaromatic in the first ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. Salicylic acid undergoes ESPT only in the "antiaromatic" S ( ππ*) state, but not in the "aromatic" S ( ππ*) state. Stokes' shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird's rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation. |
| Author | Karas, Lucas José Wu, Chia-Hua Ottosson, Henrik Wu, Judy I-Chia |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31554699$$D View this record in MEDLINE/PubMed https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-396721$$DView record from Swedish Publication Index |
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| Issue | 41 |
| Keywords | antiaromaticity hydrogen bonding Baird’s rule excited-state proton transfer aromaticity |
| Language | English |
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| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Author contributions: C.-H.W. and J.I.W. designed research; C.-H.W. and L.J.K. performed research; C.-H.W., L.J.K., H.O., and J.I.W. analyzed data and made intellectual contributions to the development of the paper; and J.I.W. wrote the paper. Edited by Kendall N. Houk, University of California, Los Angeles, CA, and approved August 28, 2019 (received for review May 20, 2019) |
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| Snippet | Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2]... Baird's rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4 + 2]... Excited-state proton transfer (ESPT) is universally recognized as a reaction that relaxes the energy of a photoexcited organic compound. It is commonly found... Baird's rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2]... Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4 n + 2]... |
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| SubjectTerms | antiaromaticity Aromatic compounds aromaticity Baird's rule Bonding strength Chemical bonds Electrons Excitation excited-state proton transfer Hydrogen Hydrogen bonding Hydrogen bonds Hydroxyquinolines - chemistry Light effects Models, Molecular Molecular Structure Organic chemistry Organic compounds Photoexcitation Physical Sciences Protons Quantum Theory Salicylic acid Salicylic Acid - chemistry Substrates Tautomers |
| Title | Excited-state proton transfer relieves antiaromaticity in molecules |
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