Roaming-mediated ultrafast isomerization of geminal tri-bromides in the gas and liquid phases
‘Roaming’ is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments ‘roam’ on a flat region of the potentia...
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| Published in | Nature chemistry Vol. 7; no. 7; pp. 562 - 568 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
01.07.2015
Nature Publishing Group |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1755-4330 1755-4349 1755-4349 |
| DOI | 10.1038/nchem.2278 |
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| Abstract | ‘Roaming’ is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments ‘roam’ on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr
3
. We see that, upon S
0
–S
1
excitation, gas-phase CHBr
3
isomerizes within 100 fs into the BrHCBr–Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr
3
and PBr
3
in solution upon S
1
excitation. Quantum chemical simulations of XBr
3
(X = B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S
1
/S
0
conical intersections and can best be described as occurring through roaming-mediated pathways.
Roaming — a new and unusual reaction mechanism in gas-phase chemical transformations — is now shown to occur in solution. Following ultraviolet excitation of geminal tribromides, what initially seems to be the simple fission of a bond is in fact isomerization occurring through the roaming of molecular fragments. |
|---|---|
| AbstractList | 'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments 'roam' on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr3. We see that, upon S0-S1 excitation, gas-phase CHBr3 isomerizes within 100 fs into the BrHCBr-Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr3 and PBr3 in solution upon S1 excitation. Quantum chemical simulations of XBr3 (X = B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S1/S0 conical intersections and can best be described as occurring through roaming-mediated pathways.'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments 'roam' on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr3. We see that, upon S0-S1 excitation, gas-phase CHBr3 isomerizes within 100 fs into the BrHCBr-Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr3 and PBr3 in solution upon S1 excitation. Quantum chemical simulations of XBr3 (X = B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S1/S0 conical intersections and can best be described as occurring through roaming-mediated pathways. 'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments 'roam' on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr3 . We see that, upon S0 -S1 excitation, gas-phase CHBr3 isomerizes within 100 fs into the BrHCBr-Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr3 and PBr3 in solution upon S1 excitation. Quantum chemical simulations of XBr3 (X = B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S1 /S0 conical intersections and can best be described as occurring through roaming-mediated pathways. 'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments 'roam' on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr sub(3). We see that, upon S sub(0)-S sub(1) excitation, gas-phase CHBr sub(3) isomerizes within 100fs into the BrHCBr-Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr sub(3) and PBr sub(3) in solution upon S sub(1) excitation. Quantum chemical simulations of XBr sub(3) (X=B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S sub(1)/S sub(0) conical intersections and can best be described as occurring through roaming-mediated pathways. ‘Roaming’ is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in the gas phase. It is characterized by frustrated bond cleavage, after which the two incipient fragments ‘roam’ on a flat region of the potential energy surface before reacting with one another. Here, we provide evidence that supports roaming in the liquid phase. We are now able to explain previous solution-phase experiments by comparing them with new ultrafast transient absorption data showing the photoisomerization of gas-phase CHBr 3 . We see that, upon S 0 –S 1 excitation, gas-phase CHBr 3 isomerizes within 100 fs into the BrHCBr–Br species, which is identical to what has been observed in solution. Similar sub-100 fs isomerization is now also observed for BBr 3 and PBr 3 in solution upon S 1 excitation. Quantum chemical simulations of XBr 3 (X = B, P or CH) suggest that photochemical reactivity in all three cases studied is governed by S 1 /S 0 conical intersections and can best be described as occurring through roaming-mediated pathways. Roaming — a new and unusual reaction mechanism in gas-phase chemical transformations — is now shown to occur in solution. Following ultraviolet excitation of geminal tribromides, what initially seems to be the simple fission of a bond is in fact isomerization occurring through the roaming of molecular fragments. |
| Author | Borin, Veniamin A. Tarnovsky, Alexander N. Eyzips, Anna Mereshchenko, Andrey S. Butaeva, Evgeniia V. |
| Author_xml | – sequence: 1 givenname: Andrey S. surname: Mereshchenko fullname: Mereshchenko, Andrey S. organization: Department of Chemistry and the Center for Photochemical Sciences, Bowling Green State University – sequence: 2 givenname: Evgeniia V. surname: Butaeva fullname: Butaeva, Evgeniia V. organization: Department of Chemistry and the Center for Photochemical Sciences, Bowling Green State University – sequence: 3 givenname: Veniamin A. surname: Borin fullname: Borin, Veniamin A. organization: Department of Chemistry and the Center for Photochemical Sciences, Bowling Green State University – sequence: 4 givenname: Anna surname: Eyzips fullname: Eyzips, Anna organization: Department of Chemistry and the Center for Photochemical Sciences, Bowling Green State University – sequence: 5 givenname: Alexander N. surname: Tarnovsky fullname: Tarnovsky, Alexander N. email: atarnov@bgsu.edu organization: Department of Chemistry and the Center for Photochemical Sciences, Bowling Green State University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26100804$$D View this record in MEDLINE/PubMed |
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| Snippet | ‘Roaming’ is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in... 'Roaming' is a new and unusual class of reaction mechanism that has recently been discovered in unimolecular dissociation reactions of isolated molecules in... |
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| SubjectTerms | 119/118 140/125 639/638/440/94 639/638/440/949 639/638/440/950 Analytical Chemistry Biochemistry Bromides Chemistry Chemistry/Food Science Inorganic Chemistry Organic Chemistry Photochemicals Photochemistry Physical Chemistry Potential energy |
| Title | Roaming-mediated ultrafast isomerization of geminal tri-bromides in the gas and liquid phases |
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