From 56ce3f631bfcfd21803fe8cc2c0c6af6295f360a Mon Sep 17 00:00:00 2001 From: Snehalatha Kaliappan Date: Tue, 31 May 2022 12:26:40 +0530 Subject: Diels-alder reaction 1st version --- Diels-Alder-Reaction.html | 175 +++++++++++++++++++++++++++++++++++++++++++++ resources/1-3butadiene.mol | 24 +++++++ resources/DAproduct1.mol | 51 +++++++++++++ resources/DAproduct2.mol | 42 +++++++++++ 4 files changed, 292 insertions(+) create mode 100644 Diels-Alder-Reaction.html create mode 100644 resources/1-3butadiene.mol create mode 100644 resources/DAproduct1.mol create mode 100644 resources/DAproduct2.mol diff --git a/Diels-Alder-Reaction.html b/Diels-Alder-Reaction.html new file mode 100644 index 0000000..a9414db --- /dev/null +++ b/Diels-Alder-Reaction.html @@ -0,0 +1,175 @@ + + + + + + + + + + + + Diels Alder Reaction - General Description- + + + + + + +
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Diels Alder Reaction - General Description

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Jmol

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Note : 3D models are created using Jmol Application version 14.31.32. To use the models interactively, place the mouse over the model, hold the left mouse button, move the mouse to rotate the model and view the model from all angles. Right-click to open the context-menu and explore the features to measure the bond-length, bond-angle, dihedral angle, change style, color of atoms bonds and many more features listed

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Structure 1 (1-3butadiene.mol)

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Structure 2 (DAproduct1.mol)

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Structure 3 (DAproduct2.mol)

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+ Structure 1 (1-3butadiene.mol) + The Diels alder reaction is one of the best examples of the [4+2] Cycloaddition reaction. In this reaction, dialkene (diene with electon donating groups) and dienophile (alkene with an electron withdrawing group) upon heating react to form a cyclic compound. Always the cis conformer of the diene participates in the reaction. 1,3-Butadiene, the simplest of the diene, exists in s-trans and s-cis conformations. The s-trans conformation is preferred due to steric reasons. Due to very low rotational barrier about the central sigma bond ( 30 kJ/mol at RT), conversion to s-cis conformation is rapid. Hence less favourable s-cis conformer is available for the cycloaddition reaction. +

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+ Structure 2 (DAproduct1.mol) + Typical example for the Diels alder reaction is, 2,3-dimethyl-1,3-butadiene as diene and 2-propenaldehyde as dienophile react to form a 6-membered cyclic product. Here, two new sigma bonds are formed and a single bonds converts to a double bond. The transition state resembles a 6-membered aromatic ring. +

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+ Structure 3 (DAproduct2.mol) + Another common example is the reaction between 1,3-butadiene and maleic anhydride. This reaction gives a bicyclic product. +

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+ + diff --git a/resources/1-3butadiene.mol b/resources/1-3butadiene.mol new file mode 100644 index 0000000..682eaae --- /dev/null +++ b/resources/1-3butadiene.mol @@ -0,0 +1,24 @@ +string +__Jmol-14_05112218313D 1 1.00000 0.00000 0 +Jmol version 14.31.32 2021-02-06 23:16 EXTRACT: ({0:2 6 14:19}) + 10 9 0 0 0 0 999 V2000 + -0.1165 0.0426 0.0350 C 0 0 0 0 0 0 + 0.2152 1.4322 0.2376 C 0 0 0 0 0 0 + -1.3507 -0.4428 0.2186 C 0 0 0 0 0 0 + 1.4494 1.9176 0.0540 C 0 0 0 0 0 0 + -0.5771 2.1064 0.5527 H 0 0 0 0 0 0 + 2.2735 1.2872 -0.2596 H 0 0 0 0 0 0 + 1.6593 2.9680 0.2164 H 0 0 0 0 0 0 + 0.6758 -0.6316 -0.2801 H 0 0 0 0 0 0 + -2.1748 0.1877 0.5322 H 0 0 0 0 0 0 + -1.5606 -1.4931 0.0562 H 0 0 0 0 0 0 + 1 2 1 0 0 0 + 3 1 2 0 0 0 + 4 2 2 0 0 0 + 5 2 1 0 0 0 + 6 4 1 0 0 0 + 7 4 1 0 0 0 + 8 1 1 0 0 0 + 9 3 1 0 0 0 + 10 3 1 0 0 0 +M END diff --git a/resources/DAproduct1.mol b/resources/DAproduct1.mol new file mode 100644 index 0000000..6f2db57 --- /dev/null +++ b/resources/DAproduct1.mol @@ -0,0 +1,51 @@ +file:/home/snehalatha/Documents/Files-March14-2022/Jmol-mol-files/Diels-Alder... +__Jmol-14_05192211033D 1 1.00000 0.00000 0 +Jmol version 14.31.32 2021-02-06 23:16 EXTRACT: ({0:23}) + 24 22 0 0 0 0 999 V2000 + -0.0116 0.4231 0.1724 C 0 0 0 0 0 0 + 1.0505 -0.2560 0.6281 C 0 0 0 0 0 0 + -0.0975 1.8808 0.2217 C 0 0 0 0 0 0 + 3.5944 0.5177 -1.3038 C 0 0 0 0 0 0 + 3.5486 1.8500 -1.1867 C 0 0 0 0 0 0 + 3.2567 2.6793 -2.3751 C 0 0 0 0 0 0 + 0.2935 2.6583 -0.7964 C 0 0 0 0 0 0 + 3.1369 3.8950 -2.2949 O 0 0 0 0 0 0 + 3.4126 0.0050 -2.2444 H 0 0 0 0 0 0 + 3.7964 -0.1040 -0.4374 H 0 0 0 0 0 0 + 3.6898 2.3683 -0.2416 H 0 0 0 0 0 0 + -0.7326 2.4736 1.4453 C 0 0 0 0 0 0 + 0.6873 2.2400 -1.7146 H 0 0 0 0 0 0 + 0.2208 3.7423 -0.7481 H 0 0 0 0 0 0 + -1.2089 -0.2786 -0.4042 C 0 0 0 0 0 0 + 1.9026 0.2485 1.0721 H 0 0 0 0 0 0 + 1.0902 -1.3408 0.5829 H 0 0 0 0 0 0 + -1.3170 3.3658 1.1898 H 0 0 0 0 0 0 + 0.0294 2.7580 2.1793 H 0 0 0 0 0 0 + -1.4213 1.7745 1.9226 H 0 0 0 0 0 0 + -1.5221 0.1772 -1.3510 H 0 0 0 0 0 0 + -2.0513 -0.2271 0.2955 H 0 0 0 0 0 0 + -1.0089 -1.3322 -0.6047 H 0 0 0 0 0 0 + 3.1383 2.1437 -3.3289 H 0 0 0 0 0 0 + 1 2 2 0 0 0 + 3 1 1 0 0 0 + 5 4 2 0 0 0 + 6 5 1 0 0 0 + 7 3 2 0 0 0 + 8 6 2 0 0 0 + 9 4 1 0 0 0 + 10 4 1 0 0 0 + 11 5 1 0 0 0 + 12 3 1 0 0 0 + 13 7 1 0 0 0 + 14 7 1 0 0 0 + 15 1 1 0 0 0 + 16 2 1 0 0 0 + 17 2 1 0 0 0 + 18 12 1 0 0 0 + 19 12 1 0 0 0 + 20 12 1 0 0 0 + 21 15 1 0 0 0 + 22 15 1 0 0 0 + 23 15 1 0 0 0 + 24 6 1 0 0 0 +M END diff --git a/resources/DAproduct2.mol b/resources/DAproduct2.mol new file mode 100644 index 0000000..952beb5 --- /dev/null +++ b/resources/DAproduct2.mol @@ -0,0 +1,42 @@ +file:/home/snehalatha/Documents/Files-March14-2022/Jmol-mol-files/Diels-Alder... +__Jmol-14_05262216343D 1 1.00000 0.00000 0 +Jmol version 14.31.32 2021-02-06 23:16 EXTRACT: ({0:18}) + 19 18 0 0 0 0 999 V2000 + -0.3283 -0.0923 0.5524 C 0 0 0 0 0 0 + 0.4677 0.8968 0.9881 C 0 0 0 0 0 0 + -0.2546 -1.5006 0.8860 C 0 0 0 0 0 0 + 0.6973 -2.1262 1.5962 C 0 0 0 0 0 0 + 2.7988 -1.6593 -0.9015 C 0 0 0 0 0 0 + 3.7542 -2.0077 0.1505 C 0 0 0 0 0 0 + 2.7644 -0.3356 -0.9785 C 0 0 0 0 0 0 + 3.6573 0.1842 0.0567 C 0 0 0 0 0 0 + 4.2637 -0.8607 0.6551 O 0 0 0 0 0 0 + 3.7887 1.3652 0.3472 O 0 0 0 0 0 0 + 4.0123 -3.1404 0.5152 O 0 0 0 0 0 0 + -1.1319 0.1719 -0.1248 H 0 0 0 0 0 0 + 1.2867 0.7348 1.6774 H 0 0 0 0 0 0 + 0.3111 1.9149 0.6529 H 0 0 0 0 0 0 + -1.0659 -2.1027 0.4937 H 0 0 0 0 0 0 + 1.5373 -1.6076 2.0385 H 0 0 0 0 0 0 + 0.6453 -3.1963 1.7576 H 0 0 0 0 0 0 + 2.2074 -2.3910 -1.4394 H 0 0 0 0 0 0 + 2.1342 0.2932 -1.5984 H 0 0 0 0 0 0 + 1 2 2 0 0 0 + 4 3 2 0 0 0 + 6 5 1 0 0 0 + 7 5 2 0 0 0 + 8 7 1 0 0 0 + 9 8 1 0 0 0 + 10 8 2 0 0 0 + 6 9 1 0 0 0 + 11 6 2 0 0 0 + 1 3 1 0 0 0 + 12 1 1 0 0 0 + 13 2 1 0 0 0 + 14 2 1 0 0 0 + 15 3 1 0 0 0 + 16 4 1 0 0 0 + 17 4 1 0 0 0 + 18 5 1 0 0 0 + 19 7 1 0 0 0 +M END -- cgit