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Dr. Ottorino ORI Dr. Ottorino ORI Actinium Chemical Research Actinium Chemical Research Rome Rome [email protected] [email protected] WEST UNIVERSITY OF TIMI WEST UNIVERSITY OF TIMI Ș Ș OARA OARA FACULTY OF CHEMISTRY, BIOLOGY, GEOGRAPHY DEPARTMENT OF BIOLOGY DEPARTMENT OF BIOLOGY - - CHEMISTRY CHEMISTRY LAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICAL LAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICAL - - CHEMISTRY FOR CHEMISTRY FOR NANOSCIENCES & QSAR NANOSCIENCES & QSAR (CFSCNQ) (CFSCNQ) Prof. dr. dr. habil. Mihai V. PUTZ Prof. dr. dr. habil. Mihai V. PUTZ Director CFSCNQ Director CFSCNQ [email protected] [email protected]

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Page 1: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Dr. Ottorino ORIDr. Ottorino ORIActinium Chemical ResearchActinium Chemical Research

[email protected]@gmail.com

WEST UNIVERSITY OF TIMIWEST UNIVERSITY OF TIMIȘȘOARAOARAFACULTY OF CHEMISTRY, BIOLOGY, GEOGRAPHYDEPARTMENT OF BIOLOGYDEPARTMENT OF BIOLOGY--CHEMISTRYCHEMISTRYLAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICALLAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICAL--CHEMISTRY FOR CHEMISTRY FOR NANOSCIENCES & QSARNANOSCIENCES & QSAR (CFSCNQ)(CFSCNQ)

Prof. dr. dr. habil. Mihai V. PUTZProf. dr. dr. habil. Mihai V. PUTZDirector CFSCNQDirector [email protected][email protected]

Page 2: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Chemical Graph Theory is an important branch of Theoretical Chemistry.

Its basic element is the so-called molecular graph G. Vertices V(G) of this graph denote molecular atoms and edges E(G) are the bonds of the molecule.

Normally, G corresponds the carbon atom skeleton of the molecule. This is the hydrogen-depleted representation of the molecular graphs. Atomic valence is the vertex degree r.

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Example Let’s consider a connected graph Glike this one with n nodes and m edges:

n =10; m =11

Chemically, G represents Naphtalene molecule with n carbon atoms and m bonds.

Vertex degree r=2 or 3 corresponds to atomic valence. For carbon, silicon compounds r≤ 4.

Page 4: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Graph Theory properties are transferred to molecular structures like the following The First Theorem of Graph Theory:

Any graph contains an even number of vertices of odd degree r

which becomes: Every molecule contains an even number of atoms of odd valence Then C61 fullerene and others with odd

carbon atoms are forbidden also by topology.

Page 5: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

In Chemical Graph Theory graph invariants or topological indices are used to correlate the properties of molecules to their chemical structure.

A topological index is defined by a map from a graph G into a number or a finite string of numbers:

Topological indices should be graph invariant, i.e. isomorphic graphs lead to the same topological index.

Page 6: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Isomorphic graphs

Page 7: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Isomorphic graphs EXERCISE are these graphs isomorphic ?

See: Lecture Notes on GRAPH THEORYTero Harju (2007), Department of MathematicsUniversity of Turku, FIN-20014 Turku, Finlande-mail: [email protected]

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Isomorphic graphs

Page 9: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

An important topological graph invariant the Graph Energy

See : Ivan Gutman, Bo Zhou and Boris FurtulaThe Laplacian–energy Like Invariant is an Energy Like InvariantMATCH Commun. Math. Comput. Chem. 64 (2010) 85-96ISSN 0340 - 6253 AND RELATED REFERENCES

Page 10: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Properties of the Graph Energy

Page 11: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Then the total π-electron energy of fullerenes and nanotubes is determined solely by their carbon atom content and depends very little on other structural features.

Properties of the Graph Energy for regular graphs, i.e. whit vertices with the same number of bonds (degree) r

Page 12: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Given two vertices u and v in V(G), we denote by d(u,v) or du,v the distance between u and v, i.e. the length of the shortest path connecting u and v by traveling along the graph edges (or molecular bonds).

This distance belongs to the invariants of the graphs conveying crucial information about the structure.

TECHNICALLY AND COMPUTATIONALLY THIS IS ONE OF SPECIALTIES OF Prof.PUTZ’s LAB

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1 5 9 7 3

2 6 10 8 4

After an arbitrarilyarbitrarily numbering of the nodes we calculate the length dij of the shortest path connecting pair wise the n atoms.

n=10; m=11

Some cases: d11=0 d12=d21=1 d16=d19=2 .. Etc..dmax=d14=5

Page 14: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

… composing - with all dij entries - the Matrix D of the chemical distances of G:

1 5 9 7 3

2 6 10 8 4

D 1 2 3 4 5 6 7 8 9 101 0 1 4 5 1 2 3 4 2 32 1 0 5 4 2 1 4 3 3 23 4 5 0 1 3 4 1 2 2 34 5 4 1 0 4 3 2 1 3 25 1 2 3 4 0 3 2 3 1 26 2 1 4 3 3 0 3 2 2 17 3 4 1 2 2 3 0 3 1 28 4 3 2 1 3 2 3 0 2 19 2 3 2 3 1 2 1 2 0 110 3 2 3 2 2 1 2 1 1 0

Page 15: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

D contains interesting structural information. Let’s zoom in it first by sorting its rows:1 5 9 7 3

2 6 10 8 4

D wi1 0 1 1 2 2 3 3 4 4 5 132 0 1 1 2 2 3 3 4 4 5 133 0 1 1 2 2 3 3 4 4 5 134 0 1 1 2 2 3 3 4 4 5 135 0 1 1 2 2 2 3 3 3 4 116 0 1 1 2 2 2 3 3 3 4 117 0 1 1 2 2 2 3 3 3 4 118 0 1 1 2 2 2 3 3 3 4 119 0 1 1 1 2 2 2 2 3 3 8,510 0 1 1 1 2 2 2 2 3 3 8,5

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… the action of D in possibly grouping structurally-equivalent atoms emerges:

1 5 9 7 3

2 6 10 8 4

D wi1 0 1 1 2 2 3 3 4 4 5 132 0 1 1 2 2 3 3 4 4 5 133 0 1 1 2 2 3 3 4 4 5 134 0 1 1 2 2 3 3 4 4 5 135 0 1 1 2 2 2 3 3 3 4 116 0 1 1 2 2 2 3 3 3 4 117 0 1 1 2 2 2 3 3 3 4 118 0 1 1 2 2 2 3 3 3 4 119 0 1 1 1 2 2 2 2 3 3 8,510 0 1 1 1 2 2 2 2 3 3 8,5

Page 17: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Row half-sum wi invariant provides atom-i contribution to Wiener index W of G:

W = ½ Σ ij dij

W = Σ wiw1 = 13, w5 = 11

W = 109 w9 = 8,5We call wi the Wiener weight of atom-i; let’s

zoom again in D by sorting by wi …..

1 5 9 7 3

2 6 10 8 4

Page 18: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

… the action of wi in suggesting possible most-stable atoms emerges:

1 5 9 7 3

2 6 10 8 4

D wi9 0 1 1 1 2 2 2 2 3 3 8,510 0 1 1 1 2 2 2 2 3 3 8,55 0 1 1 2 2 2 3 3 3 4 116 0 1 1 2 2 2 3 3 3 4 117 0 1 1 2 2 2 3 3 3 4 118 0 1 1 2 2 2 3 3 3 4 111 0 1 1 2 2 3 3 4 4 5 132 0 1 1 2 2 3 3 4 4 5 133 0 1 1 2 2 3 3 4 4 5 134 0 1 1 2 2 3 3 4 4 5 13

Page 19: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Exercise (HOMEWORK): for any (or all) of the below PAH structures:

Write the ADJACENCY MATRIXWrite the DISTANCE (BONDING) MATRIXCalculate the Wiener index by making use of molecular symmetry

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Much attention is devoted on FULLERENES. Luckily they admit a representation with

planar molecular graphs the Schlegel diagram

Buckminsterfullerene C60

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Planar connected graphs fulfil Euler’s theorem

C20nv n f ne 2

nv=20; ne=20*3/2=30 nf=12 where is the 12th face ? 20+12‐30=2W=500 = 20*w1

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Wiener index comutation of C20 fullerene

C20 W=500 = 20*w1w1 = 25

Shell s Atoms  k s*k1 3 32 6 123 6 184 3 125 1 5

50w i 25W=n*w i 500

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Ri-prediction of the magic LEM:

C28H4

Page 24: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Topological prediction of saturn like-fullerane C50H10 from C50D5h 10 equatorial reactive nodes (maximal wi ):

NOT BAD AT ALL FOR A PURE TOPOLOGICAL WIENER BASED NOT BAD AT ALL FOR A PURE TOPOLOGICAL WIENER BASED CALCULATIONS OF A MILLISECOND!CALCULATIONS OF A MILLISECOND!

Ri-prediction of the SATURN:

C50H10

Page 25: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

Let’s focus on the minimal vertices in green giving the minimal contribution w to wiener index W

w=8.5

Minimal vertices are distinguished atoms in a graph, they are in fact the most compactly embedded in the structure.

Now a question naturally arises: how to “measure”the ability of the remaining atoms in contributing to the overall compactness of graph G?

1 5 9 7 3

2 6 10 8 4

Page 26: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

A possible solution consists in computing the following invariant ρ:

ρ = W/Nwρ ≥ 1

ρ = 1.282

Index ρ, called topological efficiency indextopological efficiency index, first appeared in Ori Ottorino, Cataldo Franco and Graovac Ante (2009)‘ Topological Ranking of C28 Fullerenes Reactivity‘, Fullerenes, Nanotubes and Carbon Nanostructures, 17:3,308 — 323.

1 5 9 7 3

2 6 10 8 4

Page 27: Actinium Chemical Research Rome ottorino.ori@gmailmvputz.iqstorm.ro/upload/TOPO-Chemistry_NANO-Chemistry... · 2014-03-06 · Dr. Ottorino ORI Actinium Chemical Research Rome ottorino.ori@gmail.com

It is very interesting noticing that for the the buckminsterfullerene C60 Ih we have:

ρ = 1

C60 is in fact a very round hollow cage showing, for any of the N=60 nodes, the same {bim}={3 6 8 10 10 10 8 3 1} coordination shells with M=9; wi=139=w and therefore W=N*w=8340. In this stable structure any node works as minimal minimal nodenode.

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Assuming ρ as a measure of sphericity it gives interesting (and sometime unexpected) results:

Benzene is spherical ρ =1; Closed square lattice (torus) is spherical Closed graphene lattice is spherical Sodalite closed zeolitic lattice is spherical ρ =1 too and so onand so on……..

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Assuming ρ to determine sphericity produces interesting (and sometime unexpected) results:

C60 is spherical ρ =1 as we said; C20 polyhedron is also spherical ρ =1

Other fullerenes Cn have ρ >1 so less spherical than C20 but surely more stable Warning: better we try correlating ρ and

relative stability only among isomers of the same Cn fullerene.

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ρ is then the topological sphericity of a chemical graph

The lower is ρ the more spherical and stable the structure will be.

So we adopted for invariant ρ the new alias topological sphericity topological sphericity indexindex

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The minimum principle works BETTER on topological efficiency index topological efficiency index ρ ≥1 as it has been successfully tested on C66 fullerene 4478 isomers, see Topological efficiency of C66 fullerene, D. Vukicevic, F. Cataldo , O. Ori, A. Graovac, Chemical Physics Letters 501 (2011) 442–445.

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Int. J. Mol. Sci. 2011, 12(11), 7934-7949; doi:10.3390/ijms12117934Topological Anisotropy of Stone-Wales Waves in Graphenic FragmentsOttorino Ori, Franco Cataldo and Mihai V. Putz

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Index ρ has been put in FULLERENE generator program by Prof. Peter Schwerdtfeger

http://ctcp.massey.ac.nz/index.php?group=&page=fullerenes&menu=fullerenes

free DOWNLAOD PLS USE IT

Indices W and Indices W and ρρ tool quickly sieve interesting candidates tool quickly sieve interesting candidates for stable chemical structures (molecules, 1for stable chemical structures (molecules, 1--22--3D 3D lattices, fractalslattices, fractals……))

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Questions ?

Ottorino ORIActinium Chemical Research

[email protected]

WEST UNIVERSITY OF TIMIWEST UNIVERSITY OF TIMIȘȘOARAOARAFACULTY OF CHEMISTRY, BIOLOGY, GEOGRAPHYDEPARTMENT OF BIOLOGYDEPARTMENT OF BIOLOGY--CHEMISTRYCHEMISTRYLAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICALLAB. OF STRUCTURAL AND COMPUTATIONAL PHYSICAL--CHEMISTRY FOR CHEMISTRY FOR NANOSCIENCES & QSARNANOSCIENCES & QSAR (CFSCNQ)(CFSCNQ)

Prof. dr. dr. habil. Mihai V. PUTZProf. dr. dr. habil. Mihai V. PUTZDirector CFSCNQDirector [email protected][email protected]