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What is quasi-aromaticity?

Determining aromaticity of compoundsWhat is Y-aromaticity? Is the trinitromethanide anion aromatic?How are odor and electronic structure related to aromaticity?How does the cyclopropyl group influence conjugation and aromaticity?Aromaticity of annulenesAromaticity of multi annuli systemsAromaticity of two rings connected by double bondUnderstanding AromaticityHow is the aromaticity in graphene different from the aromaticity in benzene?Why is porphyrin aromatic?

11

1

$begingroup$

During my study of aromaticity, I came through this topic of quasi-aromaticity. Can you please elaborate what Quasi aromatic compounds are and how are they designated?

aromatic-compounds aromaticity

share|improve this question

edited May 27 at 18:29

chail10

asked May 24 at 20:26

chail10chail10

476417

$endgroup$

• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  $begingroup$
  Consider using google for such terminology. It has might show good results and is recommended before asking a question. If it is not, then the question is welcome.
  $endgroup$
  – user79161
  May 24 at 20:32
  
  

  
  
  
  


• 
  
  
  

  
  4
  

  
  
  
  
  
  

  
  $begingroup$
  This appears to be the original paper: Lloyd, D.; Marshall, D. R. Quasi-aromatic compounds: a definition, Chem. Ind. (London) 1964, 1760. Also, there is a modern review by Krygowski et al. (PDF). Feel free to improve and narrow-down your question in the meantime.
  $endgroup$
  – andselisk♦
  May 24 at 21:15
  

  
  
  
  


• 
  
  
  

  
  5
  

  
  
  
  
  
  

  
  $begingroup$
  @user79161 I completely disagree. We definitely welcome many questions that could "just be Googled." Many of these questions may bring users to less reputable sites like Yahoo answers. If we build up a repository of easily-Googled questions, we start showing up in Google which really grows our site. And it helps people get an authoritative answer.
  $endgroup$
  – Melanie Shebel♦
  May 25 at 7:10
  

  
  
  
  


• 
  
  
  

  
  3
  

  
  
  
  
  
  

  
  $begingroup$
  @MelanieShebel This site "shows on Google" more then sci. papers, so that point is moot. While the fact that something can be googled isn't a reason to close a question, because like everything here can be, users should still provide some context and introduction into the topic in the body of question, otherwise downvotes are are proper reaction.
  $endgroup$
  – Mithoron
  May 25 at 22:15
  

  
  
  
  

add a comment | 

11

1

$begingroup$

During my study of aromaticity, I came through this topic of quasi-aromaticity. Can you please elaborate what Quasi aromatic compounds are and how are they designated?

aromatic-compounds aromaticity

share|improve this question

edited May 27 at 18:29

chail10

asked May 24 at 20:26

chail10chail10

476417

$endgroup$

• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  $begingroup$
  Consider using google for such terminology. It has might show good results and is recommended before asking a question. If it is not, then the question is welcome.
  $endgroup$
  – user79161
  May 24 at 20:32
  
  

  
  
  
  


• 
  
  
  

  
  4
  

  
  
  
  
  
  

  
  $begingroup$
  This appears to be the original paper: Lloyd, D.; Marshall, D. R. Quasi-aromatic compounds: a definition, Chem. Ind. (London) 1964, 1760. Also, there is a modern review by Krygowski et al. (PDF). Feel free to improve and narrow-down your question in the meantime.
  $endgroup$
  – andselisk♦
  May 24 at 21:15
  

  
  
  
  


• 
  
  
  

  
  5
  

  
  
  
  
  
  

  
  $begingroup$
  @user79161 I completely disagree. We definitely welcome many questions that could "just be Googled." Many of these questions may bring users to less reputable sites like Yahoo answers. If we build up a repository of easily-Googled questions, we start showing up in Google which really grows our site. And it helps people get an authoritative answer.
  $endgroup$
  – Melanie Shebel♦
  May 25 at 7:10
  

  
  
  
  


• 
  
  
  

  
  3
  

  
  
  
  
  
  

  
  $begingroup$
  @MelanieShebel This site "shows on Google" more then sci. papers, so that point is moot. While the fact that something can be googled isn't a reason to close a question, because like everything here can be, users should still provide some context and introduction into the topic in the body of question, otherwise downvotes are are proper reaction.
  $endgroup$
  – Mithoron
  May 25 at 22:15
  

  
  
  
  

add a comment | 

$begingroup$

During my study of aromaticity, I came through this topic of quasi-aromaticity. Can you please elaborate what Quasi aromatic compounds are and how are they designated?

aromatic-compounds aromaticity

share|improve this question

edited May 27 at 18:29

chail10

asked May 24 at 20:26

chail10chail10

476417

$endgroup$

share|improve this question

edited May 27 at 18:29

chail10

asked May 24 at 20:26

chail10chail10

476417

share|improve this question

edited May 27 at 18:29

chail10

asked May 24 at 20:26

chail10chail10

476417

asked May 24 at 20:26

chail10chail10

476417

asked May 24 at 20:26

chail10chail10

476417

1 Answer
1

active

oldest

votes

14

$begingroup$

In general, we can describe a quasi aromatic compound as a compound, which is ionic in nature with a counter ion, and the $pi$ electrons in such compounds follow Huckel's rule ($4n+2$).

In other words, quasi aromatic compounds are those in which the charges present on the molecule are a part of aromaticity of the compound. A few examples of such compounds are depicted in the diagram:

However, it has a deeper and broader meaning. For a more in-depth explanation, please read the given references.

---

References:

1. T. M. Krygowski, B. Bankiewicz, Z. Czarnocki, M. Palusiak, “Quasi-aromaticity—what does it mean?” Tetrahedron 2015, 71(30), 4895–4908 (https://doi.org/10.1016/j.tet.2015.05.074).


2. E. Kleinpeter, A. Koch, “Characterization and quantification of quasi-aromaticity by spatial magnetic properties (TSNMRS),” Tetrahedron 2015, 71(33), 5275–5284 (https://doi.org/10.1016/j.tet.2015.06.019).

share|improve this answer

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

$endgroup$

• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  The references do not seem to match the answer, as the former tend to emphasize secondary bonding as part of the quasi-aromatic structure and the species do not seem to be charged. What am I missing?
  $endgroup$
  – Oscar Lanzi
  May 27 at 1:09
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  @ Oscar Lanzi: I don't think you are missing anything. I think chemists are giving broader picture to existing simple definition. All are still a theory.
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:55
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  $begingroup$
  @Melanie Shebel: Thank you for careful (and ruthless! :-)) editing. I'll also take an advantage to congratulate you for your new moderator ship!
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:58
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  Even though the gold book calls it Hückel (4n + 2) rule, there are more components to aromaticity than a simple number. Yet it appears that all that ever is taught about aromatic compounds is that number, without any limitations of the generalisation and approximation of these rules. I think it is more important to understand that all compounds that follow Hückel's rules have aromatic character, but not all compounds where aromaticity is observed follow Hückel's rules.
  $endgroup$
  – Martin - マーチン♦
  May 27 at 21:47
  

  
  
  
  

add a comment | 

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14

$begingroup$

In general, we can describe a quasi aromatic compound as a compound, which is ionic in nature with a counter ion, and the $pi$ electrons in such compounds follow Huckel's rule ($4n+2$).

In other words, quasi aromatic compounds are those in which the charges present on the molecule are a part of aromaticity of the compound. A few examples of such compounds are depicted in the diagram:

However, it has a deeper and broader meaning. For a more in-depth explanation, please read the given references.

---

References:

1. T. M. Krygowski, B. Bankiewicz, Z. Czarnocki, M. Palusiak, “Quasi-aromaticity—what does it mean?” Tetrahedron 2015, 71(30), 4895–4908 (https://doi.org/10.1016/j.tet.2015.05.074).


2. E. Kleinpeter, A. Koch, “Characterization and quantification of quasi-aromaticity by spatial magnetic properties (TSNMRS),” Tetrahedron 2015, 71(33), 5275–5284 (https://doi.org/10.1016/j.tet.2015.06.019).

share|improve this answer

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

$endgroup$

• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  The references do not seem to match the answer, as the former tend to emphasize secondary bonding as part of the quasi-aromatic structure and the species do not seem to be charged. What am I missing?
  $endgroup$
  – Oscar Lanzi
  May 27 at 1:09
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  @ Oscar Lanzi: I don't think you are missing anything. I think chemists are giving broader picture to existing simple definition. All are still a theory.
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:55
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  $begingroup$
  @Melanie Shebel: Thank you for careful (and ruthless! :-)) editing. I'll also take an advantage to congratulate you for your new moderator ship!
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:58
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  Even though the gold book calls it Hückel (4n + 2) rule, there are more components to aromaticity than a simple number. Yet it appears that all that ever is taught about aromatic compounds is that number, without any limitations of the generalisation and approximation of these rules. I think it is more important to understand that all compounds that follow Hückel's rules have aromatic character, but not all compounds where aromaticity is observed follow Hückel's rules.
  $endgroup$
  – Martin - マーチン♦
  May 27 at 21:47
  

  
  
  
  

add a comment | 

14

$begingroup$

In general, we can describe a quasi aromatic compound as a compound, which is ionic in nature with a counter ion, and the $pi$ electrons in such compounds follow Huckel's rule ($4n+2$).

In other words, quasi aromatic compounds are those in which the charges present on the molecule are a part of aromaticity of the compound. A few examples of such compounds are depicted in the diagram:

However, it has a deeper and broader meaning. For a more in-depth explanation, please read the given references.

---

References:

1. T. M. Krygowski, B. Bankiewicz, Z. Czarnocki, M. Palusiak, “Quasi-aromaticity—what does it mean?” Tetrahedron 2015, 71(30), 4895–4908 (https://doi.org/10.1016/j.tet.2015.05.074).


2. E. Kleinpeter, A. Koch, “Characterization and quantification of quasi-aromaticity by spatial magnetic properties (TSNMRS),” Tetrahedron 2015, 71(33), 5275–5284 (https://doi.org/10.1016/j.tet.2015.06.019).

share|improve this answer

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

$endgroup$

• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  The references do not seem to match the answer, as the former tend to emphasize secondary bonding as part of the quasi-aromatic structure and the species do not seem to be charged. What am I missing?
  $endgroup$
  – Oscar Lanzi
  May 27 at 1:09
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  @ Oscar Lanzi: I don't think you are missing anything. I think chemists are giving broader picture to existing simple definition. All are still a theory.
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:55
  

  
  
  
  


• 
  
  
  

  
  2
  

  
  
  
  
  
  

  
  $begingroup$
  @Melanie Shebel: Thank you for careful (and ruthless! :-)) editing. I'll also take an advantage to congratulate you for your new moderator ship!
  $endgroup$
  – Mathew Mahindaratne
  May 27 at 20:58
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  Even though the gold book calls it Hückel (4n + 2) rule, there are more components to aromaticity than a simple number. Yet it appears that all that ever is taught about aromatic compounds is that number, without any limitations of the generalisation and approximation of these rules. I think it is more important to understand that all compounds that follow Hückel's rules have aromatic character, but not all compounds where aromaticity is observed follow Hückel's rules.
  $endgroup$
  – Martin - マーチン♦
  May 27 at 21:47
  

  
  
  
  

add a comment | 

$begingroup$

In general, we can describe a quasi aromatic compound as a compound, which is ionic in nature with a counter ion, and the $pi$ electrons in such compounds follow Huckel's rule ($4n+2$).

In other words, quasi aromatic compounds are those in which the charges present on the molecule are a part of aromaticity of the compound. A few examples of such compounds are depicted in the diagram:

However, it has a deeper and broader meaning. For a more in-depth explanation, please read the given references.

---

References:

1. T. M. Krygowski, B. Bankiewicz, Z. Czarnocki, M. Palusiak, “Quasi-aromaticity—what does it mean?” Tetrahedron 2015, 71(30), 4895–4908 (https://doi.org/10.1016/j.tet.2015.05.074).


2. E. Kleinpeter, A. Koch, “Characterization and quantification of quasi-aromaticity by spatial magnetic properties (TSNMRS),” Tetrahedron 2015, 71(33), 5275–5284 (https://doi.org/10.1016/j.tet.2015.06.019).

share|improve this answer

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

$endgroup$

share|improve this answer

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

edited May 27 at 20:46

Melanie Shebel♦

3,47673273

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131

answered May 24 at 21:38

Mathew MahindaratneMathew Mahindaratne

8,3911131