Are there amide versions of lactides and lactones?











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In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










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  • 1




    By the way, there are also lactols.
    – mykhal
    2 days ago















up vote
3
down vote

favorite












In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










share|improve this question


















  • 1




    By the way, there are also lactols.
    – mykhal
    2 days ago













up vote
3
down vote

favorite









up vote
3
down vote

favorite











In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.










share|improve this question













In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $alpha$-hydroxy; and $gamma$- or $delta$- hydroxy carboxylic acids; respectively, are esterified.



Now, there exists a certain similarity between amides and esters (both being carboxylic acid-derivatives), such as the similarity between ester bonds in polyesters and amide bonds in polyamides.



In this context, I have a question: Do amides have compounds similar to lactides and lactones? What are they commonly known as?



Please let me know a good source that I could refer to in addition to any answers posted, or please cite any sources used.







organic-chemistry esters amides






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asked 2 days ago









AbhigyanC

956326




956326








  • 1




    By the way, there are also lactols.
    – mykhal
    2 days ago














  • 1




    By the way, there are also lactols.
    – mykhal
    2 days ago








1




1




By the way, there are also lactols.
– mykhal
2 days ago




By the way, there are also lactols.
– mykhal
2 days ago










1 Answer
1






active

oldest

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up vote
6
down vote













Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






share|improve this answer



















  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    2 days ago






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    2 days ago










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    yesterday











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1 Answer
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active

oldest

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1 Answer
1






active

oldest

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active

oldest

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active

oldest

votes








up vote
6
down vote













Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






share|improve this answer



















  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    2 days ago






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    2 days ago










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    yesterday















up vote
6
down vote













Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






share|improve this answer



















  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    2 days ago






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    2 days ago










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    yesterday













up vote
6
down vote










up vote
6
down vote









Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.






share|improve this answer














Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013):




P-66.1.5.1 Lactams and lactims



Intramolecular amides of amino carboxylic acids, $ce{-CO-NHbond{-}}$, are
called ‘lactams’ and their tautomers, $ce{-C(OH)=Nbond{-}}$, are ‘lactims’. Lactams named in two ways:



  (1) as heterocyclic pseudoketones;



  (2) by substituting ‘lactam’ for the ‘ic acid’ ending of the systematic ‘oic acid’ name for the parent acid without the amino substituent, and inserting a locant designating the position of the amino group between the ‘o’ and the ‘lactam’. Method ‘lactams’. Lactims are named in the same way, using ‘lactim’ in place of ‘lactam’.



(1) generates preferred IUPAC names.



Examples:



Fig.1



pyrrolidin-2-one (PIN)

butano-4-lactam



(…)



enter image description here



3,4,5,6-tetrahydropyridin-2-ol (PIN)

pentano-5-lactim




(Note that the numberings depicted are for the preferred names (PINs) based on nitrogen heterocyclics)



There's no (at least IUPAC) term for lactides analogue (‘lactide’ is not used in IUPAC names themselves anyway), but they exist.



In traditional or general names, the Greek letter numbering is used, e.g. ε-caprolactam, or β-lactam four-membered ring part in bicyclic penicillin skeleton.







share|improve this answer














share|improve this answer



share|improve this answer








edited 2 days ago

























answered 2 days ago









mykhal

3,65912054




3,65912054








  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    2 days ago






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    2 days ago










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    yesterday














  • 2




    Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
    – Mathew Mahindaratne
    2 days ago






  • 1




    @MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
    – AbhigyanC
    2 days ago










  • @AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
    – Mithoron
    yesterday








2




2




Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
– Mathew Mahindaratne
2 days ago




Lactide is a cyclic lactone di-ester, derived from lactic acid (en.wikipedia.org/wiki/Lactide). Thus, there is no name for lactam version. However, it could be a series of derivatives of piperazine-2,5-diones. Simplest member is piperazine-2,5-dione, derived from glycine.
– Mathew Mahindaratne
2 days ago




1




1




@MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
– AbhigyanC
2 days ago




@MathewMahindaratne Can you please add an answer? It seems comments eventually get deleted... This is good enough for an answer.
– AbhigyanC
2 days ago












@AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
– Mithoron
yesterday




@AbhigyanC They need to obsolete/not useful etc. and flagged (or deleted by author). I'd expect comments that add important stuff to answer to last.
– Mithoron
yesterday


















 

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