ΜΕΛΕΤΗ ΣΥΜΠΛΟΚΩΝ ΚΥΚΛΟΔΕΞΤΡΙΝΩΝ
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- Λέων Ζέρβας
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1 ΜΕΛΕΤΗ ΣΥΜΠΛΟΚΩΝ ΚΥΚΛΟΔΕΞΤΡΙΝΩΝ 1) File --> open --> /.../4cpa.cif 2) Περιοχή: Structure Navigator --> Crystal Structures --> 4cpa 3) Περιοχή: Display options --> More Info Space group:... ( * )Z:, Z : 4) Παρατηρήστε τη θερμική κίνηση του μοντέλου επιλέγοντας: Style Ellipsoid ή/και Colour Atomic displacement 5) Ανοίξτε το 4cpa.cif με έναν text editor (π.χ. wordpad) και σβήστε τη θέση (Β) με αριθμό κατάληψης 36% (θα αναγνωρίσετε τα άτομα από το όνομα τους που περιέχει το Β αλλά και από τον αριθμό κατάληψης τους που είναι 0.36). Αποθηκεύεστε το αρχείο με διαφορετικό όνομα π.χ. 4CPA_A.cif και ανοίξτε με mercury το νέο αυτό αρχείο. Τώρα θα πρέπει να βλέπετε ξεκάθαρα μόνο μία θέση guest. 4) ΔΙΑΜΟΡΦΩΣΗ ΜΟΡΙΟΥ ΞΕΝΙΣΤΗ (β-κυκλοδεξτρίνη) i) Ενδομοριακοί Υδρογονικοί δεσμοί; * For many discrete-molecule materials, the molecules pack together to form crystals in a relatively simple way determined by the Space Group. Such materials are said to have Z'=1 (Z-prime). Increasingly, crystallographers are beginning to find crystals in which the basic building block is not just one molecule, but several molecules taken together. Such materials are said to have Z'>1.
2 Ο22... Ο31 Απόσταση (Å) Γωνία ( ) ii) Conformational characteristics of the.-cd/ complex Residue n=1 n=2 n=3 n=4 n=5 n=6 n=7.. D (Å) Φ h ( ) d (Å) D K (Å) τ (º) ω(º) Conformation (Παράρτημα Ι i ) D = O4n O4(n+1) distances; Φ h = O4(n-1) O4n O4(n+1) angles; d = deviations of the O4n atoms from their least-squares plane; D k = KA O4nA; τ = tilt angles between the optimum O4n plane and the mean plane of the O4(n-1), C1n, C4n, O4n atoms; torsion angles ω = O5n-C5n-C6n-O6n; conformation of the primary hydroxyls iii) ΣΧΗΜΑΤΙΣΜΟΣ ΔΙΜΕΡΟΥΣ Περιοχή: Display options --> Packing
3 (Menu) Calculate --> Packing/Slicing --> a: b: c: Υδρογονικοί δεσμοί για σχηματισμό διμερούς συμπλόκων κατά τον άξονα b Απόσταση (Å) Γωνία ( ) Ο31... Ο3 7 5) ΔΙΑΜΟΡΦΩΣΗ ΞΕΝΙZOMENOY MOPIOY (4CPA) 5.1 Καρβοξύλιο (H-bonds με νερά έξω από cavity) 5.2 Etheric O 5.3 phenyl groups (pi-pi) - Shortest inter-phenyl carbon-carbon distance (SICD) = ( gia to C5A- C5A) [Hunter, 1990 rule 3.4<SICD<4.8] - centroids distance = offset(πυθαγορειο) = 1.68 (διαμετρος phenyl~2.78) 5.4 Cl (location: O2,O3 plane, H-bond entrapped water molecule)
4 6) ΑΛΛΗΛΕΠΙΔΡΑΣΕΙΣ ΞΕΝΙΣΤΗ ΞΕΝΙΖΟΜΕΝΟΥ CH-π interactions (ΠΑΡΑΡΤΗΜΑ ΙΙ ii ) ================= H:... C1:... C2:... ω =... θ =... Dpln=... Dlin =... Datm =... Region =...
5 6) ΔΙΚΤΥΟ ΥΔΡΟΓΟΝΙΚΩΝ ΔΕΣΜΩΝ - ΝΕΡΑ
6 7) CRYSTAL PACKING
7 *i ΠΑΡΑΡΤΗΜΑ I Glucose is a highly complex chemical compound because it can exist is many isomeric forms and each isomer is subject to rotational isomerism. Within the cyclic form of glucose, rotation may occur around the O6-C6-C5-O5 torsion angle, termed the ω-angle, to form three rotamer conformations as shown in the diagram below. In referring to the orientations of the ω-angle and the O6-C6-C5- C4 angle, the three stable staered rotamer conformations are termed gauche-gauche (), gauche-trans () and trans-gauche (tg). For methyl α-d-glucopyranose at equilibrium the ratio of molecules in each rotamer conformation is reported as 57 : 38 : 5 : : tg. Kirschner, Karl N.; Woods, Robert J. (2001), "Solvent interactions determine carbohydrate conformation", Proc. Natl. Acad. Sci. USA 98 (19): This tendency for the ω-angle to prefer to adopt a gauche conformation is attributed to the gauche effect. (The term "gauche" refers to conformational isomers (conformers) where two vicinal (In chemistry vicinal (from Latin vicinus = neighbor) stands for any two functional groups bonded to two adjacent carbon atoms) groups are separated by a 60 torsion angle). Rotation around the C-5/C-6 bond is described by the angle ω. Three possible staered conformations possible; gauche-trans (), gauche-gauche (), trans-gauche(tg). Example Conformational characteristics of the α-cd/camphor complexes Residue n=1 n=2 n=3 n=4 n=5 n=6 R-αCD ω (º) Conformation a b 76.7 a 60.4 b 75.2 a 62.6 b 90.5 a b 80.8 c a b 80.3 a -52 b 64.8 c In stereochemistry, gauche interactions hinder bond rotation. For example, sighting along the C5-C6 bond, there are two possible relative potential energies. Τhe conformational families about the C 5 C 6 bond display a bias for gauche orientations. In general a gauche rotamer (, -HO(6) points outwards the CyD cavity) is less stable than an anti-rotamer ( - -HO(6) points inwards the CyD cavity).
8 ii ΠΑΡΑΡΤΗΜΑ ΙΙ CH/p Interactions as Demonstrated in the Crystal Structure of Host/Guest Compounds. A Database Study Hiroki Takahashi, Sei Tsuboyama, Yoji Umezawa, Kazumasa Honda and Motohiro Nishio Tetrahedron 56 (2000) CH/ interactions: O: centre of plane. C 1 and C 2 : nearest and second nearest sp 2 -carbons, respectively, to H. : dihedral angle defined by C 1 OC 2 and H C 1 C 2 planes. : angle HXC 1 D pln : H/ -plane distance (H/I) D atm : interatomic distance (H/C 1 ) D lin : distance between H and line C 1 C 2 (H/J) D max = Å Region 1 D pln < D max < 60 Region 2 D lin < D max < < < 130 Region 3 D atm < D max < < < 90 ( : HC 1 I)
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