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What is “mechanistic duality�
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I am doing a general overview of different kinds of dualities present in science. I am quite well versed with the dualities in physics and mathematics. I was searching for dualities in chemistry, biology and other sciences. In that process, I encountered "mechanistic duality" in chemistry. For instance, see [1] and [2].
But I am not able to find a good introduction or description about "mechanisitic duality". It would also be nice if someone can briefly explain what this duality mean. Does someone have clue about its history (who coined it first and for what purpose)? Also, please point me to relevant book/paper which discuss this.
Denmark, S. E.; Su, X.; Nishigaichi, Y. The Chemistry of Trichlorosilyl Enolates. 6. Mechanistic Duality in the Lewis Base-Catalyzed Aldol Addition Reaction. J. Am. Chem. Soc. 1998, 120 (49), 12990–12991. DOI: 10.1021/ja982993v.
Ross, S. P.; Baire, B.; Hoye, T. R. Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels–Alder Benzynes. Org. Lett. 2017, 19 (20), 5705–5708. DOI: 10.1021/acs.orglett.7b02888.
reaction-mechanism terminology
edited 38 mins ago
Martin - マーãƒÂン♦
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werunom
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up vote
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I am doing a general overview of different kinds of dualities present in science. I am quite well versed with the dualities in physics and mathematics. I was searching for dualities in chemistry, biology and other sciences. In that process, I encountered "mechanistic duality" in chemistry. For instance, see [1] and [2].
But I am not able to find a good introduction or description about "mechanisitic duality". It would also be nice if someone can briefly explain what this duality mean. Does someone have clue about its history (who coined it first and for what purpose)? Also, please point me to relevant book/paper which discuss this.
Denmark, S. E.; Su, X.; Nishigaichi, Y. The Chemistry of Trichlorosilyl Enolates. 6. Mechanistic Duality in the Lewis Base-Catalyzed Aldol Addition Reaction. J. Am. Chem. Soc. 1998, 120 (49), 12990–12991. DOI: 10.1021/ja982993v.
Ross, S. P.; Baire, B.; Hoye, T. R. Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels–Alder Benzynes. Org. Lett. 2017, 19 (20), 5705–5708. DOI: 10.1021/acs.orglett.7b02888.
reaction-mechanism terminology
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
asked 1 hour ago
werunom
211
New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
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up vote
4
down vote
favorite
up vote
4
down vote
favorite
I am doing a general overview of different kinds of dualities present in science. I am quite well versed with the dualities in physics and mathematics. I was searching for dualities in chemistry, biology and other sciences. In that process, I encountered "mechanistic duality" in chemistry. For instance, see [1] and [2].
But I am not able to find a good introduction or description about "mechanisitic duality". It would also be nice if someone can briefly explain what this duality mean. Does someone have clue about its history (who coined it first and for what purpose)? Also, please point me to relevant book/paper which discuss this.
Denmark, S. E.; Su, X.; Nishigaichi, Y. The Chemistry of Trichlorosilyl Enolates. 6. Mechanistic Duality in the Lewis Base-Catalyzed Aldol Addition Reaction. J. Am. Chem. Soc. 1998, 120 (49), 12990–12991. DOI: 10.1021/ja982993v.
Ross, S. P.; Baire, B.; Hoye, T. R. Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels–Alder Benzynes. Org. Lett. 2017, 19 (20), 5705–5708. DOI: 10.1021/acs.orglett.7b02888.
reaction-mechanism terminology
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
asked 1 hour ago
werunom
211
New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
I am doing a general overview of different kinds of dualities present in science. I am quite well versed with the dualities in physics and mathematics. I was searching for dualities in chemistry, biology and other sciences. In that process, I encountered "mechanistic duality" in chemistry. For instance, see [1] and [2].
But I am not able to find a good introduction or description about "mechanisitic duality". It would also be nice if someone can briefly explain what this duality mean. Does someone have clue about its history (who coined it first and for what purpose)? Also, please point me to relevant book/paper which discuss this.
Denmark, S. E.; Su, X.; Nishigaichi, Y. The Chemistry of Trichlorosilyl Enolates. 6. Mechanistic Duality in the Lewis Base-Catalyzed Aldol Addition Reaction. J. Am. Chem. Soc. 1998, 120 (49), 12990–12991. DOI: 10.1021/ja982993v.
Ross, S. P.; Baire, B.; Hoye, T. R. Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels–Alder Benzynes. Org. Lett. 2017, 19 (20), 5705–5708. DOI: 10.1021/acs.orglett.7b02888.
reaction-mechanism terminology
reaction-mechanism terminology
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
asked 1 hour ago
werunom
211
New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
asked 1 hour ago
werunom
211
New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
edited 38 mins ago
Martin - マーãƒÂン♦
32.8k9102219
32.8k9102219
asked 1 hour ago
werunom
211
New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 1 hour ago
werunom
211
asked 1 hour ago
werunom
211
211
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werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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New contributor
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
werunom is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
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1 Answer
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This just means that the same type of reaction may proceed by two different mechanisms depending on the exact chemical being used. It's not a particularly widely used term (it is not a "standard" phrase such as wave-particle duality) and there are many other ways of saying the same thing ("divergence", "pathway", etc.).
As an extremely simple example, alkyl bromides can react with nucleophiles via either an SN1 or SN2 pathway, depending on the degree of substitution of the carbon bonded to bromine. This is an example of how a different substrate may follow a different mechanism, although the end result is the same (replacement of Br with the nucleophile).
The papers you cited are just slightly more sophisticated examples of the same concept.
answered 1 hour ago
orthocresol♦
36.1k7105211
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
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1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
up vote
5
down vote
This just means that the same type of reaction may proceed by two different mechanisms depending on the exact chemical being used. It's not a particularly widely used term (it is not a "standard" phrase such as wave-particle duality) and there are many other ways of saying the same thing ("divergence", "pathway", etc.).
As an extremely simple example, alkyl bromides can react with nucleophiles via either an SN1 or SN2 pathway, depending on the degree of substitution of the carbon bonded to bromine. This is an example of how a different substrate may follow a different mechanism, although the end result is the same (replacement of Br with the nucleophile).
The papers you cited are just slightly more sophisticated examples of the same concept.
answered 1 hour ago
orthocresol♦
36.1k7105211
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
add a comment |Â
up vote
5
down vote
This just means that the same type of reaction may proceed by two different mechanisms depending on the exact chemical being used. It's not a particularly widely used term (it is not a "standard" phrase such as wave-particle duality) and there are many other ways of saying the same thing ("divergence", "pathway", etc.).
As an extremely simple example, alkyl bromides can react with nucleophiles via either an SN1 or SN2 pathway, depending on the degree of substitution of the carbon bonded to bromine. This is an example of how a different substrate may follow a different mechanism, although the end result is the same (replacement of Br with the nucleophile).
The papers you cited are just slightly more sophisticated examples of the same concept.
answered 1 hour ago
orthocresol♦
36.1k7105211
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
add a comment |Â
up vote
5
down vote
up vote
5
down vote
This just means that the same type of reaction may proceed by two different mechanisms depending on the exact chemical being used. It's not a particularly widely used term (it is not a "standard" phrase such as wave-particle duality) and there are many other ways of saying the same thing ("divergence", "pathway", etc.).
As an extremely simple example, alkyl bromides can react with nucleophiles via either an SN1 or SN2 pathway, depending on the degree of substitution of the carbon bonded to bromine. This is an example of how a different substrate may follow a different mechanism, although the end result is the same (replacement of Br with the nucleophile).
The papers you cited are just slightly more sophisticated examples of the same concept.
answered 1 hour ago
orthocresol♦
36.1k7105211
This just means that the same type of reaction may proceed by two different mechanisms depending on the exact chemical being used. It's not a particularly widely used term (it is not a "standard" phrase such as wave-particle duality) and there are many other ways of saying the same thing ("divergence", "pathway", etc.).
As an extremely simple example, alkyl bromides can react with nucleophiles via either an SN1 or SN2 pathway, depending on the degree of substitution of the carbon bonded to bromine. This is an example of how a different substrate may follow a different mechanism, although the end result is the same (replacement of Br with the nucleophile).
The papers you cited are just slightly more sophisticated examples of the same concept.
answered 1 hour ago
orthocresol♦
36.1k7105211
edited 1 hour ago
answered 1 hour ago
orthocresol♦
36.1k7105211
answered 1 hour ago
orthocresol♦
36.1k7105211
answered 1 hour ago
orthocresol♦
36.1k7105211
36.1k7105211
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
add a comment |Â
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
Thanks! So, if I have got you right, "mechanistic duality" is the presence of two different "mechanisms" through which a given reactants produce the same end product. Here, I have few clarifications 1) are there only two pathways? and if so why? 2) In other words, can there be cases where for a given reactants, there can be n number of pathways to end with the same outcome? 3) Is there any general theory which decides the number of pathways for the particular kind of inputs? Excuse! I am completely new to this area. Also, any reference you can point to will be of great help.
– werunom
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
(1) It depends on the exact case. Two is not a special number in and of itself. (2) Yes, hydrolysis of esters is a good example, with at least three possible mechanisms that I can think of. (3) Yes, it's called chemistry. Generally there are some mechanisms which are considered plausible and some which are considered implausible. To find and identify these, you need to apply principles of chemistry which you have learnt - not just one principle, but many of them, accrued over years of study. Unfortunately, there is no real shortcut.
– orthocresol♦
1 hour ago
add a comment |Â
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